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Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones

  1. Ryoji Noyori Prof. Dr.,
  2. Takeshi Ohkuma Assoc. Prof. Dr.

Article first published online: 4 JAN 2001

DOI: 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 40, Issue 1, pages 40–73, January 5, 2001

Additional Information

How to Cite

Noyori, R. and Ohkuma, T. (2001), Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones. Angew. Chem. Int. Ed., 40: 40–73. doi: 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5

Author Information

  1. Department of Chemistry and Research Center for Materials Science Nagoya University Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-783-4177

Publication History

  1. Issue published online: 4 JAN 2001
  2. Article first published online: 4 JAN 2001
  3. Manuscript Received: 10 JAN 2000

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    S. Itsuno , M. Nakano , K. Miyazaki , H. Masuda , K. Ito , A. Hirao , S. Nakahama , J. Chem. Soc. Perkin Trans. 1 1985, 2039–2044.
  • 53
    T. Imai , T. Tamura , A. Yamamuro , T. Sato , T. A. Wollmann , R. M. Kennedy , S. Masamune , J. Am. Chem. Soc. 1986, 108, 7402–7404.
  • 54
     
  • 54a
    I. Ojima, K. Hirai in ref [14a], Vol. 5, chap 4;
  • 54b
    H. Brunner, H. Nishiyama, K. Itoh in ref [3c], chap 6;
  • 54c
    H. Brunner in ref [14b], Vol. E21d, pp. 4074–4081;
  • 54d
    H. Brunner in ref [1m], Vol. 2, pp. 131–140;
  • 54e
    H. Nishiyama in ref [3f], Vol. 1, pp. 267–287.
  • 55
     
  • 55a
    H. Brunner , R. Becker , G. Riepl , Organometallics 1984, 3, 1354–1359;
  • 55b
    H. Nishiyama , M. Kondo , T. Nakamura , K. Itoh , Organometallics 1991, 10, 500–508;
  • 55c
    J. Sakaki , W. B. Schweizer , D. Seebach , Helv. Chim. Acta 1993, 76, 2654–2665;
    Direct Link:
  • 55d
    M. Sawamura , R. Kuwano , Y. Ito , Angew. Chem. 1994, 106, 92–93;
    Direct Link:
    Angew. Chem. Int. Ed. Engl. 1994, 33, 111–113;
    Direct Link:
  • 55e
    M. B. Carter , B. Schiøtt , A. Gutiérrez , S. L. Buchwald , J. Am. Chem. Soc. 1994, 116, 11 667–11 670;
  • 55f
    Y. Nishibayashi , K. Segawa , H. Takada , K. Ohe , S. Uemura , Chem. Commun. 1996, 847–848;
  • 55g
    D. K. Heldmann , D. Seebach , Helv. Chim. Acta 1999, 82, 1096–1110;
    Direct Link:
  • 55h
    J. Yun , S. L. Buchwald , J. Am. Chem. Soc. 1999, 121, 5640–5644.
  • 56
     
  • 56a
    J. D. Morrison , H. S. Mosher in Asymmetric Organic Reactions, Prentice-Hall, New Jersey, 1971, chap 5;
  • 56b
    U. Matteoli , P. Frediani , M. Bianchi , C. Botteghi , S. Gladiali , J. Mol. Catal. 1981, 12, 265–319;
  • 56c
    G. Zassinovich , G. Mestroni , S. Gladiali , Chem. Rev. 1992, 92, 1051–1069;
  • 56d
    C. F. de Graauw , J. A. Peters , P. H. van Bekkum , J. Huskens , Synthesis 1994, 1007–1017;
  • 56e
    K. Krohn in ref [14b], Vol. E21d, pp. 4099–4142;
  • 56f
    S. Gladiali, G. Mestroni in ref [1m], Vol. 2, pp. 97–119;
  • 56g
    M. J. Palmer , M. Wills , Tetrahedron: Asymmetry 1999, 10, 2045–2061.
  • 57a
    D. Müller , G. Umbricht , B. Weber , A. Pfaltz , Helv. Chim. Acta 1991, 74, 232–239;
    Direct Link:
  • 57b
    D. A. Evans , S. G. Nelson , M. R. Gagné , A. R. Muci , J. Am. Chem. Soc. 1993, 115, 9800–9801;
  • 57c
    T. Langer , G. Helmchen , Tetrahedron Lett. 1996, 37, 1381–1384.
  • 58
     
  • 58a
    R. Noyori , S. Hashiguchi , Acc. Chem. Res. 1997, 30, 97–102;
  • 58b
    M. J. Palmer , M. Willis , Tetrahedron: Asymmetry 1999, 10, 2045–2061.
  • 59
     
  • 59a
    Reduction: Techniques and Applications in Organic Synthesis (Ed.: R. L. Augustine), Marcel Dekker, New York, 1968;
  • 59b
    Stereoselective Reductions (Benchmark Papers in Organic Chemistry, Vol. 6) (Eds.: M. P. Doyle, C. T. West), Dowden, Hutchinson & Ross, Stroudsburg, Pennsylvania, 1976;
  • 59c
    M. Hudlický , Reductions in Organic Chemistry, 2nd ed., American Chemical Society, Washington, DC, 1996;
  • 59d
    Reductions in Organic Synthesis: Recent Advances and Practical Applications (Ed.: A. F. Abdel-Magid), American Chemical Society, Washington, 1996 (ACS Symp. Ser. 1996, 641);
  • 59e
    J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed., Wiley-VCH, New York, 1997
  • 60
    Reviews:
  • 60a
    E. R. Grandbois, S. I. Howard, J. D. Morrison in ref [14a], Vol. 2, chap 3;
  • 60b
    Y. Inouye, J. Oda, N. Baba in ref [14a], Vol. 2, chap 4;
  • 60c
    H. Haubenstock , Top. Stereochem. 1983, 14, 231–300;
  • 60d
    M. Nishizawa , R. Noyori in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 159–182;
  • 60e
    M. M. Midland, L. A. Morell in ref [14b], Vol. E21d, pp. 4049–4066;
  • 60f
    see ref [15h], chap 3;
  • 60g
    see ref [15i], chap 6;
  • 60h
    see ref [15k], chap 7;
  • 60i
    A. K. Beck, R. Dahinden, F. N. M. Kühnle in ref [59d], chap 3;
  • 60j
    see ref [59e], pp. 55–65.
  • 61
     
  • 61a
    M. L. H. Green , G. Parkin , K. J. Moynihan , K. Prout , J. Chem. Soc. Chem. Commun. 1984, 1540;
  • 61b
    S. Shambayati , W. E. Crowe , S. L. Schreiber , Angew. Chem. 1990, 102, 273–290;
    Direct Link:
    Angew. Chem. Int. Ed. Engl. 1990, 29, 256–272;
    Direct Link:
  • 61c
    S. Shambayati , S. L. Schreiber in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, Oxford, 1991, pp. 283–324.
  • 62
     
  • 62a
    Selectivities in Lewis Acid Promoted Reactions (Ed.: D. Schinzer), Kluwer, Dordrecht, 1988;
  • 62b
    M. Santelli , J.-M. Pons , Lewis Acids and Selectivity in Organic Synthesis, CRC Press, Boca Raton, FL, USA, 1996;
  • 62c
    Lewis Acid Reagents: A Practical Approach (Ed.: H. Yamamoto), Oxford University Press, Oxford, 1999.
  • 63
     
  • 63a
    Y.-H. Huang , J. A. Gladysz , J. Chem. Educ. 1988, 65, 298–303;
  • 63b
    J. A. Gladysz , B. J. Boone , Angew. Chem. 1997, 109, 566–602;
    Direct Link:
    Angew. Chem. Int. Ed. Engl. 1997, 36, 550–583.
    Direct Link:
  • 64
    For example:
  • 64a
    see ref [1d], chap 5;
  • 64b
    see ref [1i], chap 6.
  • 65
     
  • 65a
    M. Yamakawa , R. Noyori , J. Am. Chem. Soc. 1995, 117, 6327–6335;
  • 65b
    M. Yamakawa , R. Noyori , Organometallics 1999, 18, 128–133.
  • 66a
    D. S. Matteson , Organomet. Chem. Rev. A 1969, 4, 263–305;
  • 66b
    D. A. Evans , Science 1988, 240, 420–426;
  • 66c
    E. J. Corey , P.-W. Yuen , F. J. Hannon , D. A. Wierda , J. Org. Chem. 1990, 55, 784–786;
  • 66d
    H. Steinhagen , G. Helmchen , Angew. Chem. 1996, 108, 2489–2492;
    Direct Link:
    Angew. Chem. Int. Ed. Engl. 1996, 35, 2339–2342.
    Direct Link:
  • 67
    M. Nakamura , E. Nakamura , N. Koga , K. Morokuma , J. Am. Chem. Soc. 1993, 115, 11 016–11 017.
  • 68
    M. Tokunaga, Dissertation, Nagoya University, 1995.
  • 69
     
  • 69a
    M. Bartók , Stereochemistry of Heterogeneous Metal Catalysis, Wiley, Chichester, 1985;
  • 69b
    Handbook of Heterogeneous Catalysis, Vol. 1–5 (Eds.: G. Ertl, H. Knözinger, J. Weitkamp), VCH, Weinheim, 1997;
  • 69c
    J. M. Thomas , W. J. Thomas , Principles and Practice of Heterogeneous Catalysis, VCH, Weinheim, 1997;
  • 69d
    “Heterogeneous Catalysis and Fine Chemicals IV”: Stud. Surf. Sci. Catal. 1997, 108;
  • 69e
    “Science and Technology in Catalysis 1998”: Stud. Surf. Sci. Catal. 1999, 121.
  • 70
     
  • 70a
    H. B. Kagan in ref [14a], Vol. 5, chap 1;
  • 70b
    H. Brunner , Top. Stereochem. 1988, 18, 129–247;
  • 70c
    H.-U. Blaser , Chem. Rev. 1992, 92, 935–952;
  • 70d
    D. J. Ager , I. Prakash , D. R. Schaad , Chem. Rev. 1996, 96, 835–875;
  • 70e
    L. Schwink , P. Knochel , Chem. Eur. J. 1998, 4, 950–968;
    Direct Link:
  • 70f
    C. J. Richards , A. J. Locke , Tetrahedron: Asymmetry 1998, 9, 2377–2407;
  • 70g
    D. Lucet , T. Le Gall , C. Mioskowski , Angew. Chem. 1998, 110, 2724–2772;
    Direct Link:
    Angew. Chem. Int. Ed. 1998, 37, 2580–2627.
    Direct Link:
  • 71
    Acceleration of Ru-catalyzed CO2 hydrogenation with a small amount of H2O or CH3OH was explained by this mechanism. See: P. G. Jessop , Y. Hsiao , T. Ikariya , R. Noyori , J. Am. Chem. Soc. 1996, 118, 344–355.
  • 72
    Certain chiral Lewis acid/Brønsted acid combined systems can be used for asymmetric protonation: K. Ishihara , S. Nakamura , M. Kaneeda , H. Yamamoto , J. Am. Chem. Soc. 1996, 118, 12 854–12 855.
  • 73
    Examples:
  • 73a
    B. Rosenberg , L. Van Camp , E. B. Grimley , A. J. Thomson , J. Biol. Chem. 1967, 242, 1347–1352;
  • 73b
    J. Reedijk , Inorg. Chim. Acta 1992, 198–200, 873–881;
  • 73c
    Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy 2 (Eds.: H. M. Pinto, J. H. Schornagel), Plenum, New York, 1996;
  • 73d
    Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), Wiley-VCH, Weinheim, 1999;
  • 73e
    E. Wong , C. M. Giandomenico , Chem. Rev. 1999, 99, 2451–2466;
  • 73f
    E. R. Jamieson , S. J. Lippard , Chem. Rev. 1999, 99, 2467–2498;
  • 73g
    J. Reedijk , Chem. Rev. 1999, 99, 2499–2510;
  • 73h
    Z. Guo , P. J. Sadler , Angew. Chem. 1999, 111, 1610–1630;
    Direct Link:
    Angew. Chem. Int. Ed. 1999, 38, 1512–1531.
    Direct Link:
  • 74
    T. Ohkuma , H. Ooka , S. Hashiguchi , T. Ikariya , R. Noyori , J. Am. Chem. Soc. 1995, 117, 2675–2676.
  • 75
    J. Takehara , S. Hashiguchi , A. Fujii , S. Inoue , T. Ikariya , R. Noyori , Chem. Commun. 1996, 233–234.
  • 76
    For the concept of ligand-accelerated catalysis see: D. J. Berrisford , C. Bolm , K. B. Sharpless , Angew. Chem. 1995, 107, 1159–1171;
    Direct Link:
    Angew. Chem. Int. Ed. Engl. 1995, 34, 1059–1070.
    Direct Link:
  • 77
    see for example:
  • 77a
    H. D. Kaesz , R. B. Saillant , Chem. Rev. 1972, 72, 231–281;
  • 77b
    D. S. Moore , S. D. Robinson , Chem. Soc. Rev. 1983, 12, 415–452.
  • 78
    J.-E. Bäckvall , R. L. Chowdhury , U. Karlson , G.-Z. Wang in Perspectives in Coordination Chemistry (Eds.: A. F. Williams, C. Floriani, A. E. Merbach), VHCA, Basel, 1992, pp. 463–486, and refs therein.
  • 79
    H. Doucet , T. Ohkuma , K. Murata , T. Yokozawa , M. Kozawa , E. Katayama , A. F. England , T. Ikariya , R. Noyori , Angew. Chem. 1998, 110, 1792–1796;
    Direct Link:
    Angew. Chem. Int. Ed. 1998, 37, 1703–1707.
    Direct Link:
  • 80
    S. Cenini , F. Porta , M. Pizzotti , J. Mol. Catal. 1982, 15, 297–308.
  • 81
    Preparation of trans-[RuCl2{P(C6H5)3}2{NH2(CH2)2NH2}]: [RuCl2{P(C6H5)3}3] (1.11 g, 1.16 mmol) was placed in a 50-mL Schlenk flask in which the air had been replaced with argon. CH2Cl2 (10 mL) and NH2(CH2)2NH2 (0.15 mL, 2.2 mmol) were then added. The mixture was degassed with three cycles of vacuum and argon replacement and was stirred at 25 °C for 3 h. After removal of turbidity by filtration, the filtrate was concentrated to ca. 5 mL, hexane (20 mL) was then added and a light brown powder was obtained. The supernatant solution was removed and the resulting solid was dried under reduced pressure (1 Torr) to give analytically pure trans-[RuCl2{P(C6H5)3}2{NH2(CH2)2NH2}] (0.55 g, 63 % yield). Decomposition point (DP): 176 °C; IR (KBr): equation image [cm−1]: 3220, 3320 (H-N); 1H NMR (400 MHz, C6D6, 25 °C, TMS): δ=2.1 (m, 4 H; 2CH2), 2.8 (m, 4 H; 2NH2), 6.8–8.0 (m, 30 H; aromatics); 31P NMR (81 MHz, C6D6, 10 % H3PO4 as external standard) δ=45.5 (s).
  • 82
    In order to obtain high catalytic activity, particularly in the reaction of a high S/C value, the substrate should be washed with a base solution prior to use.
  • 83
    T. Ohkuma , M. Koizumi , H. Ikehira , T. Yokozawa , R. Noyori , Org. Lett. 2000, 2, 659–662.
  • 84
     
  • 84a
    V. K. Pendse , B. R. Madan , Indian J. Physiol. Pharmacol. 1969, 13, 29–36;
  • 84b
    P. A. J. Janssen , FR-B 2 014 487, 1970 [Chem. Abstr. 1971, 74, 53848s];
  • 84c
    E. Regel , W. Draber , K. H. Büchel , M. Plempel , DE-B 2 461 406, 1976 [Chem. Abstr. 1976, 85, 160095t];
  • 84d
    F. Awouters , C. J. E. Niemegeers , J. Van den Berk , J. M. Van Nueten , F. M. Lenaerts , M. Borgers , K. H. L. Schellekens , A. Broeckaert , J. De Cree , P. A. J. Janssen , Experientia 1977, 33, 1657–1659;
  • 84e
    K. Meguro , M. Aizawa , T. Sohda , Y. Kawamatsu , A. Nagaoka , Chem. Pharm. Bull. 1985, 33, 3787–3797.
  • 85
     
  • 85a
    K. Bowden , M. Hardy , Tetrahedron 1966, 22, 1169–1174;
  • 85b
    G. T. Bruce , A. R. Cooksey , K. J. Morgan , J. Chem. Soc. Perkin Trans. 2 1975, 551–553; see also: H. C. Brown , O. H. Wheeler , K. Ichikawa , Tetrahedron 1957, 1, 214–220.
  • 86
    Reviews:
  • 86a
    H. C. Brown , S. Krishnamurthy , Tetrahedron 1979, 35, 567–607;
  • 86b
    N. Greeves in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1–24;
  • 86c
    see ref [59c], chap 13;
  • 86d
    H. C. Brown, P. V. Ramachandran in ref [59d], chap 1;
  • 86e
    see ref [59e], chap 3.
  • 87
    Reviews:
  • 87a
    R. L. Augustine , Adv. Catal. 1976, 25, 56–80;
  • 87b
    E. Keinan , N. Greenspoon in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 523–578.
  • 88
     
  • 88a
    J. M. Grosselin , C. Mercier , G. Allmang , F. Grass , Organometallics 1991, 10, 2126–2133;
  • 88b
    B. Cornils , W. A. Herrmann , R. W. Eckl , J. Mol. Catal. A Chemical 1997, 116, 27–33.
  • 89
    Other examples with homogeneous catalysts:
  • 89a
    K. Hotta , J. Mol. Catal. 1985, 29, 105–107;
  • 89b
    K. Hotta , Kagaku to Kogyo (Tokyo) 1986, 60, 196–205 (Chemistry and Chemical Industry);
  • 89c
    E. Farnetti , M. Pesce , J. Kaspar , R. Spogliarich , M. Graziani , J. Mol. Catal. 1987, 43, 35–40.
  • 90
    With heterogeneous catalysts:
  • 90a
    W. F. Tuley , R. Adams , J. Am. Chem. Soc. 1925, 47, 3061–3068;
  • 90b
    S. Galvagno , Z. Poltarzewski , A. Donato , G. Neri , R. Pietropaolo , J. Chem. Soc. Chem. Commun. 1986, 1729–1731;
  • 90c
    Y. Nitta , Y. Hiramatsu , T. Imanaka , Chem. Express 1989, 4, 281–284;
  • 90d
    Y. Nitta , Y. Hiramatsu , T. Imanaka , J. Catal. 1990, 126, 235–245;
  • 90e
    A. Giroir-Fendler , D. Richard , P. Gallezot , Catal. Lett. 1990, 5, 175–181;
  • 90f
    J. M. Planeix , N. Coustel , B. Coq , V. Brotons , P. S. Kumbhar , R. Dutartre , P. Geneste , P. Bernier , P. M. Ajayan , J. Am. Chem. Soc. 1994, 116, 7935–7936.
  • 91
    With polymer-bound rhodium catalysts:
  • 91a
    K. Kaneda , T. Mizugaki , Organometallics 1996, 15, 3247–3249;
  • 91b
    T. Mizugaki , Y. Kanayama , K. Ebitani , K. Kaneda , J. Org. Chem. 1998, 63, 2378–2381.
  • 92
    E. Farnetti , J. Kašpar , R. Spogliarich , M. Graziani , J. Chem. Soc. Dalton Trans. 1988, 947–952.
  • 93
    K. Mashima , T. Akutagawa , X. Zhang , H. Takaya , T. Taketomi , H. Kumobayashi , S. Akutagawa , J. Organomet. Chem. 1992, 428, 213–222.
  • 94
    J. F. Daeuble , J. M. Stryker in Catalysis of Organic Reactions (Eds.: M. G. Scaros, M. L. Prunier), Marcel Dekker, New York, 1995, pp. 235–247.
  • 95
    C. S. Chin , B. Lee , S. C. Park , J. Organomet. Chem. 1990, 393, 131–135.
  • 96
    Heterogeneous hydrogenation:
  • 96a
    P. S. Gradeff , G. Formica , Tetrahedron Lett. 1976, 4681–4684;
  • 96b
    J. Ishiyama , S. Maeda , K. Takahashi , Y. Senda , S. Imaizumi , Bull. Chem. Soc. Jpn. 1987, 60, 1721–1726.
  • 97
    T. Ohkuma , H. Ooka , T. Ikariya , R. Noyori , J. Am. Chem. Soc. 1995, 117, 10 417–10 418.
  • 98
    D. Evans , J. A. Osborn , F. H. Jardine , G. Wilkinson , Nature 1965, 208, 1203–1204.
  • 99
    1-Phenyl-3-butyn-1-one, an α,β-acetylenic ketone, could not be hydrogenated under such conditions.
  • 100
    Recent reviews: A. P. Davis in ref. [14b], Vol. E21d, pp. 3988–4048. Reduction with dissolving metals: A. M. El-Khawaga, H. M. R. Hoffmann in ref. [14b], Vol.  E21d, pp. 3967–3987; reduction with metal alkoxides: K. Krohn in ref. [14b], Vol. E21d, pp. 4099–4142.
  • 101
    Highly diastereoselective Selectride reduction:
  • 101a
    H. C. Brown , S. Krishnamurthy , J. Am. Chem. Soc. 1972, 94, 7159–7161;
  • 101b
    S. Krishnamurthy , H. C. Brown , J. Am. Chem. Soc. 1976, 98, 3383–3384.
  • 102
    G. Boireau , A. Deberly , R. Toneva , Synlett 1993, 585–587.
  • 103
     
  • 103a
    E. L. Eliel , R. J. L. Martin , D. Nasipuri , Org. Synth. Coll. Vol. 1973, 5, 175–178;
  • 103b
    G. B. Fisher , J. C. Fuller , J. Harrison , S. G. Alvarez , E. R. Burkhardt , C. T. Goralski , B. Singaram , J. Org. Chem. 1994, 59, 6378–6385;
  • 103c
    M. C. Barden , J. Schwartz , J. Org. Chem. 1995, 60, 5963–5965;
  • 103d
    G. Godjoian, G. B. Fisher, C. T. Goralsky, B. Singaram in ref [59d], chap 10.
  • 104
    T. Ohkuma , H. Ooka , M. Yamakawa , T. Ikariya , R. Noyori , J. Org. Chem. 1996, 61, 4872–4873.
  • 105
    Hydrogenation of 4-tert-butylcyclohexanone with a [RuCl2{P(C6H5)3}3]/NH2(CH2)2NH2/KOH catalyst system: Half molar 2-propanol solutions of NH2(CH2)2NH2 (39 mL, 0.0195 mmol) and KOH (78 mL, 0.038 mmol) were added to 2-propanol (5 mL) in a 20-mL Schlenk flask. The solution was degassed by three freeze-thaw cycles. Solid [RuCl2{P(C6H5)3}3] (18.7 mg, 0.0195 mmol) was added to the diamine/KOH solution under a stream of argon, and the resultant mixture was further degassed by two freeze-thaw cycles, sonicated for 30 min, and used as a catalyst stock solution. 2-Propanol (100 mL) charged into a second 250-mL Schlenk flask by hypodermic syringe and was also degassed. Solid 4-tert-butylcyclohexanone (30.0 g, 194.5 mmol) was placed into a 500-mL glass autoclave equipped with a Teflon-coated magnetic stirring bar, a pressure gauge, and a gas inlet tube attached to a hydrogen source. 2-Propanol and the catalyst solution were subsequently transferred by cannula to the autoclave. Hydrogen was introduced initially into the autoclave at a pressure of 4 atm and was then reduced to 1 atm by carefully releasing the stop valve. After repeating this procedure five times, the vessel was pressurized to 4 atm. The reaction mixture was vigorously stirred at 28 °C for 80 h, during which time the open hydrogen cylinder remained connected. After this time, the yield and cis:trans ratio as determined by GC analysis (TC-WAX (polyethylene glycol) column) were 99.8 % and 98.4:1.6, respectively. After the hydrogen gas was carefully vented, the solvent was removed under reduced pressure. The residue was purified by distillation giving cis-4-tert-butylcyclohexanol (98.3 % pure, 29.2 g, 96 % yield), BP: 112–115 °C (19 Torr). Recrystallization of this product from a water–ethanol mixture gave 99.6 % pure compound (23.4 g, 82 % yield).
  • 106
     
  • 106a
    S. Tomoda , T. Senju , Tetrahedron 1997, 53, 9057–9066;
  • 106b
    S. Tomoda , Chem. Rev. 1999, 99, 1243–1263.
  • 107
     
  • 107a
    S. Mitsui , H. Saito , Y. Yamashita , M. Kaminaga , Y. Senda , Tetrahedron 1973, 29, 1531–1539;
  • 107b
    S. Nishimura , M. Ishige , M. Shiota , Chem. Lett. 1977, 963–966.
  • 108
    M. Balasubramanian , A. D'Souza , Tetrahedron 1968, 24, 5399–5408.
  • 109
    Examples of other catalytic stereoselective methods. Transfer hydrogenation:
  • 109a
    H. B. Henbest , T. R. B. Mitchell , J. Chem. Soc. C 1970, 785–791;
  • 109b
    K. Konishi , T. Aida , S. Inoue , J. Org. Chem. 1990, 55, 816–820. Hydrosilylation:
  • 109c
    I. Ojima , M. Nihonyanagi , Y. Nagai , Bull. Chem. Soc. Jpn. 1972, 45, 3722;
  • 109d
    M. F. Semmelhack , R. N. Misra , J. Org. Chem. 1982, 47, 2469–2471;
  • 109e
    M. Fujita , T. Hiyama , J. Org. Chem. 1988, 53, 5405–5415. Hydrostannation:
  • 109f
    J.-P. Quintard , M. Pereyre , Bull. Soc. Chim. Fr. 1972, 1950–1955.
  • 110
     
  • 110a
    E. L. Eliel , N. L. Allinger , S. J. Angyal , G. A. Morrison , Conformational Analysis, Wiley, New York, 1965;
  • 110b
    E. L. Eliel , S. H. Wilen , L. N. Mander , Stereochemistry of Organic Compounds, Wiley, New York, 1994;
  • 110c
    Conformational Behavior of Six-Membered Rings: Analysis, Dynamics, and Stereoelectronic Effects (Ed.: E. Juaristi), VCH, New York, 1995.
  • 111
     
  • 111a
    see ref [110a], pp. 112–121;
  • 111b
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    M. Emura , T. Toyota , N. Seido , M. Harada , R. Noyori , T. Ikariya , T. Ohkuma , JP-A 241195, 1997 [Chem. Abstr. 1997, 127, 292919k].
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    Preparation of trans-[RuCl2{(R)-binap}{(R,R)-dpen}]: [{RuCl2(benzene)}2] (129 mg, 0.258 mmol) and (R)-BINAP (341 mg, 0.55 mmol) were placed in a 50-mL Schlenk flask. After the air in the flask was replaced with argon, DMF (9 mL) was added to the flask, the mixture was degassed by three cycles of vacuum and argon replacement and then heated at 100 °C for 10 min while stirred giving a reddish brown solution. After the solution was cooled to 25 °C, (R,R)-DPEN (117 mg, 0.55 mmol) was added and the mixture was stirred for 3 h. DMF was removed under reduced pressure (1 Torr) at 25 °C and then at 50 °C. The residue was resolved in CH2Cl2 (10 mL) and turbidity was removed by filtration. The filtrate was concentrated to ca. 1 mL, then ether (10 mL) was added and a light brown powder was obtained. The supernatant was removed and the resulting solid was dried under reduced pressure to give analytically pure trans-[RuCl2{(R)-binap}{(R,R)-dpen}] (0.34 g, 66 % yield). DP: 235 °C; IR: equation image [cm−1]: 3225, 3320 (H-N); 1H NMR (400 MHz): δ=3.3 (m, 2 H, 2 NHH), 3.45 (m, 2 H, 2NHH), 4.55 (m, 2 H, 2NH2CH), 6.3–8.8 (m, 42 H, aromatics); 31P NMR (81 MHz, C6D6, 10 % H3PO4 as external standard) δ=47.4 (s).
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  • 126
    For the sake of formal consistency, the Scheme lists results obtained with an (S)-diphosphane/(S)- or (S,S)-diamine combined system. Some experiments were actually performed by using the enantiomeric catalyst.
  • 127
    Asymmetric hydrogenation of acetophenone using trans-[RuCl2{(S)-tolbinap}{(S,S)-dpen}]: 2-Propanol (20 mL) charged into a 100-mL Schlenk flask was degassed by three vacuum–nitrogen replacement cycles. Solid trans-[RuCl2{(S)-tolbinap}{(S,S)-dpen}] (22 mg, 0.020 mmol) was dissolved in the 2-propanol and used as a catalyst stock solution. Acetophenone (601 g, 5.0 mol) and solid (CH3)3COK (5.6 g, 0.050 mol) were placed in a 10-L stainless steel autoclave. Air present in the autoclave was replaced by nitrogen. 2-Propanol (1.5 L) and an aliquot of the catalyst solution (2.0 mL, 0.002 mmol; molar ratio ketone:Ru:base=2 400 000:1:24 000) were added to the autoclave under a stream of nitrogen. The mixture was degassed by three cycles of vacuum–nitrogen replacement. Hydrogen was introduced initially into the autoclave at a pressure of 10 atm and then reduced to 1 atm by carefully releasing the stop valve. After this procedure was repeated three times, the vessel was pressurized to 45 atm. The reaction mixture was vigorously stirred for 48 h at 30 °C to give R-enriched 1-phenylethanol. The yield and ee value determined by GC (Cyclodextrin-β-236M column) were 100 and 80 %, respectively. After the hydrogen gas was carefully vented, the solvent was removed under reduced pressure. The residue was passed through silica gel (300 g) eluting with ethyl acetate, and then distilled to give (R)-1-phenylethanol (577 g, 94 % yield). Bp: 99 °C (15 Torr); [α]equation image=+38.1° (c=1.02, CH2Cl2).
  • 128
    T. Ohkuma , M. Koizumi , H. Doucet , T. Pham , M. Kozawa , K. Murata , E. Katayama , T. Yokozawa , T. Ikariya , R. Noyori , J. Am. Chem. Soc. 1998, 120, 13 529–13 530.
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  • 133
    S. Kan, unpublished results from our laboratories .
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  • 140
    Asymmetric hydrogenation of o-chlorobenzophenone with trans-[RuCl2{(S)-xylbinap}{(S)-daipen}]: Solid trans-[RuCl2{(S)-xylbinap}{(S)-daipen}] (28.7 mg, 0.0235 mmol) and o-chlorobenzophenone (101.8 g, 0.47 mol) were placed in a 1.5-L stainless steel autoclave equipped with a mechanical stirring blade, a pressure gauge, and a gas inlet tube attached to a hydrogen source. Air in the autoclave was replaced by argon. 2-Propanol (150 mL) and a 1.0 M (CH3)3COK solution in tert-butyl alcohol (4.7 mL, 4.7 mmol) were added to the autoclave under a stream of argon. The mixture was degassed by three cycles of vacuum–argon replacement. The vessel was pressurized with H2 to 8 atm, and then the reaction mixture was vigorously stirred for 55 h at 30 °C. The yield and ee value of (S)-o-chlorobenzhydrol determined by GC (HP-INNOWax (polyethylene glycol) column) and chiral HPLC (CHIRALCEL OD column) analysis were 99 and 97 %, respectively. After the hydrogen gas was carefully vented, the solvent was removed under reduced pressure. Distillation of the residue gave the S alcohol (97.5 g, 95 % yield). Bp: 138–139 °C (0.3 Torr); [α]equation image=−21.51° (c=1.14, CHCl3).
  • 141
    Asymmetric reduction using silicon- and boron-based hydrides:
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    Asymmetric hydrogenation of 2-acetylfuran with trans-[RuCl2{(R)-xylbinap}{(R)-daipen}]: Solid trans-[RuCl2{(R)-xylbinap}{(R)-daipen}] (30.5 mg, 0.025 mmol) and 2-acetylfuran (110.1 g, 1.00 mol) were placed in a 1.5-L stainless steel autoclave equipped with a mechanical stirring blade, a pressure gauge, and a gas inlet tube attached to a hydrogen source. Air present in the autoclave was replaced by argon. 2-Propanol (100 mL) and a 1.0 M (CH3)3COK solution in tert-butyl alcohol (7.5 mL, 7.5 mmol) were added to the autoclave under a stream of argon. The mixture was degassed by three cycles of vacuum-filling with argon. The vessel was pressurized to 50 atm, and then the reaction mixture was vigorously stirred for 22 h at 24 °C. The yield and ee values of (S)-1-(2-furyl)ethanol determined by GC analysis (HP-INNOWax and Chirasil-DEX CB columns) were 96 and 99 %, respectively. After the hydrogen gas was carefully vented, the solvent was removed under reduced pressure. Distillation of the residue gave (S)-1-(2-furyl)ethanol (92.8 g, 83 % yield). Bp: 76 °C (18 Torr); [α]equation image=−20.1° (c=1.00, CHCl3).
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