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  • 1
    See, for example:
  • 1a
    M. E. Jung in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp. 167;
  • 1b
    V. J. Lee in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp. 69137;
  • 1c
    V. J. Lee in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp. 139168;
  • 1d
    J. A. Kozlowski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp. 169198;
  • 1e
    K. Bauer, D. Garbe, H. Surburg in Common Fragrance and Flavor Materials, Wiley-VCH, Weinheim, 2001;
  • 1f
    S. P. Marsden in Science of Synthesis, Vol. 26 (Ed.: J. Cossy), Thieme Verlag, Stuttgart, 2004, pp. 10451121;
  • 1g
    I. Escher, F. Glorius in Science of Synthesis, Vol. 25 (Eds.: R. Brückner, E. Schaumann), Thieme Verlag, Stuttgart, 2006, pp. 733777.
  • 2
    J. Clayden, N. Greeves, S. Warren, P. Wothers in Organic Chemistry, Oxford University Press, Oxford, 2001.
  • 3
    For review articles highlighting the concept of atom economy, see:
  • 3a
    B. M. Trost, Science 1991, 254, 14711477;
  • 3b
    B. M. Trost, Angew. Chem. 1995, 107, 285307; Angew. Chem. Int. Ed. Engl. 1995, 34, 259281;
  • 3c
    R. A. Sheldon, Pure Appl. Chem. 2000, 72, 12331246;
  • 3d
    B. M. Trost, Acc. Chem. Res. 2002, 35, 695705;
  • 3e
    B. M. Trost, M. U. Frederiksen, M. T. Rudd, Angew. Chem. 2005, 117, 67886825; Angew. Chem. Int. Ed. 2005, 44, 66306666;
  • 3f
    R. A. Sheldon, Green Chem. 2007, 9, 12731283.
  • 4
    K. H. Meyer, K. Schuster, Ber. Dtsch. Chem. Ges. 1922, 55, 819823.
  • 5
    For early reviews, see:
  • 5a
    S. A. Vartanyan, S. O. Babanyan, Russ. Chem. Rev. 1967, 36, 670686;
  • 5b
    S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429438.
  • 6
    H. Rupe, E. Kambli, Helv. Chim. Acta 1926, 9, 672.
    Direct Link:
  • 7
    For reviews on metal-catalyzed Meyer–Schuster rearrangements, see:
  • 7a
    D. A. Engel, G. B. Dudley, Org. Biomol. Chem. 2009, 7, 41494158;
  • 7b
    V. Cadierno, P. Crochet, S. E. García-Garrido, J. Gimeno, Dalton Trans. 2010, 39, 40154031.
  • 8
    A protocol for the selective Meyer–Schuster rearrangement of propargylic alcohols using boronic acids as catalysts under mild conditions has been recently disclosed: H. Zheng, M. Lejkowski, D. G. Hall, Chem. Sci. 2011, 2, 13051310.
  • 9
     
  • 9a
    V. Cadierno, J. Díez, S. E. García-Garrido, J. Gimeno, N. Nebra, Adv. Synth. Catal. 2006, 348, 21252132;
  • 9b
    J. Borge, V. Cadierno, J. Díez, S. E. García-Garrido, J. Gimeno, Dyes Pigm. 2010, 87, 209217.
  • 10
     
  • 10a
    B. Alcaide, P. Almendros, M. T. Quirós, Adv. Synth. Catal. 2011, 353, 585594;
  • 10b
    R. Sarma, D. Prajapati, Synlett 2008, 30013005;
  • 10c
    K. C. Lekhok, D. Prajapati, R. C. Boruah, Synlett 2008, 655658.
  • 11
    K. A. Nolin, R. W. Ahn, Y. Kobayashi, J. J. Kennedy-Smith, F. D. Toste, Chem. Eur. J. 2010, 16, 95559562.
  • 12
     
  • 12a
    C. J. Rieder, K. J. Winberg, F. G. West, J. Am. Chem. Soc. 2009, 131, 75047505;
  • 12b
    C. J. Rieder, K. J. Winberg, F. G. West, J. Org. Chem. 2011, 76, 5056.
  • 13
     
  • 13a
    S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Chem. Asian J. 2010, 5, 141146;
  • 13b
    C. Schwehm, M. Wohland, M. E. Maier, Synlett 2010, 17891792;
  • 13c
    M. Wohland, M. E. Maier, Synlett 2011, 15231526.
  • 14
    L.-Z. Dai, M. Shi, Chem. Eur. J. 2008, 14, 55385554.
  • 15
    B. M. Trost, X. Luan, J. Am. Chem. Soc. 2011, 133, 17061709.
  • 16
    Application of metal-catalyzed Meyer–Schuster rearrangements to the synthesis of (S)-α-ionone and prostaglandins has also been described recently:
  • 16a
    M. Stefanoni, M. Luparia, A. Porta, G. Zanoni, G. G. Vidari, Chem. Eur. J. 2009, 15, 39403944;
  • 16b
    R. S. Ramón, S. Gaillard, A. M. Z. Slawin, A. Porta, A. D’Alfonso, G. Zanoni, S. P. Nolan, Organometallics 2010, 29, 36653668;
  • 16c
    G. Zanoni, A. D’Alfonso, A. Porta, L. Feliciani, S. P. Nolan, G. Vidari, Tetrahedron 2010, 66, 74727478.
  • 17
    The mechanism of the isomerization of 2-methyl-3-butyn-2-ol into 3-methyl-2-butenal, catalyzed by an oxotitanium complex, has been previously investigated by synthesizing several compounds that model the postulated metal-oxo-propargyloxo intermediate. C. Y. Lorber, M.-T. Youinou, J. Kress, J. A. Osborn, Polyhedron 2000, 19, 16931698.
  • 18
    The basis of this reaction is a [3,3]-sigmatropic transposition of the metal-oxo intermediate. Similar reactions are also known for allylic alcohols using molybdenum, vanadium, or rhenium catalysts.
  • 18a
    T. Hosogai, Y. Fujita, Y. Ninagawa, T. Nishida, Chem. Lett. 1982, 357360;
  • 18b
    S. Matsubara, T. Okazoe, K. Oshima, K. Takai, H. Nozaki, Bull. Chem. Soc. Jpn. 1985, 58, 844849;
  • 18c
    J. Belgacem, J. Kress, J. A. Osborn, J. Am. Chem. Soc. 1992, 114, 15011502;
  • 18d
    J. Belgacem, J. Kress, J. A. Osborn, J. Mol. Catal. 1994, 86, 267285;
  • 18e
    S. Bellemin-Laponnaz, H. Gisie, J. P. Le Ny, J. A. Osborn, Angew. Chem. 1997, 109, 10111013; Angew. Chem. Int. Ed. Engl. 1997, 36, 976978;
  • 18f
    S. Bellemin-Laponnaz, J. P. Le Ny, J. A. Osborn, Tetrahedron Lett. 2000, 41, 15491552;
  • 18g
    S. Akai, K. Tanimoto, Y. Kanao, M. Egi, T. Yamamoto, Y. Kita Angew. Chem. 2006, 118, 2654–2657; Angew. Chem. Int. Ed. 2006, 45, 2592–2595; Angew. Chem. Int. Ed. 2006, 45, 25922595;
  • 18h
    C. Morrill, G. L. Beutner, R. H. Grubbs, J. Org. Chem. 2006, 71, 78137825;
  • 18i
    E. C. Hansen, D. J. Lee, J. Am. Chem. Soc. 2006, 128, 81428143;
  • 18j
    A. T. Herrmann, T. Saito, C. E. Stivala, J. Tom, A. Zakarian, J. Am. Chem. Soc. 2010, 132, 59625963.
  • 19
     
  • 19a
    Variants involving the direct addition of the propargylic OH group across the M[DOUBLE BOND]O bond have also been proposed; in this case, a hydroxo–propargyloxo species [M(OH)(OCR2R3C[TRIPLE BOND]CR1)] is involved in the [3,3]-sigmatropic rearrangement: see reference [16a];
  • 19b
    Introduction of a Lewis acid cocatalyst able to coordinate to the C[TRIPLE BOND]C bond of propargylic alcohol is also known to favor the key [3,3]-sigmatropic rearrangement step: M. Egi, Y. Yamaguchi, N. Fujiwara, S. Akai, Org. Lett. 2008, 10, 18671870.
  • 20
    For a recent review, see: G. Licini, V. Conte, A. Coletti, M. Mba, C. Zonta, Coord. Chem. Rev. 2011, 255, 23452357.
  • 21
     
  • 21a
    P. Chabardes, Y. Querou, Fr. Pat. FR1554805, 1969;
  • 21b
    P. Chabardes, Y. Querou, U. S. Pat. US3920751, 1975;
  • 21c
    M. B. Erman, I. S. Aulchenko, L. A. Kheifits, V. G. Dulova, J. N. Novikov, M. E. Volpin, Tetrahedron Lett. 1976, 17, 29812984;
  • 21d
    G. L. Olson, K. D. Morgan, G. Saucy, Synthesis 1976, 2526;
  • 21e
    G. L. Olson, H.-C. Cheung, K. D. Morgan, R. Borer, G. Saucy, Helv. Chim. Acta 1976, 59, 567585;
  • 21f
    H. Pauling, D. A. Andrews, N. C. Hindley, Helv. Chim. Acta 1976, 59, 12331243;
  • 21g
    P. Chabardes, E. Kuntz, J. Varagnat, Tetrahedron 1977, 33, 17751783;
  • 21h
    P. Chabardes, E. Kuntz, Ger. Pat. DE2657335, 1977;
  • 21i
    K. Bruns, U. Weber in Flavors and Fragrances: A World Perspective, (Eds.: B. M. Lawrence, B. D. Mookherjee, B. J. Willis), Elsevier Science Publishers, Amsterdam, 1988;
  • 21j
    B. M. Choudary, A. D. Prasad, V. L. K. Valli, Tetrahedron Lett. 1990, 31, 75217522;
  • 21k
    M. B. Erman, S. E. Gulyi, I. S. Aulchenko, Mendeleev Commun. 1994, 4, 89;
  • 21l
    B. M. Trost, C. K. Chung, J. Am. Chem. Soc. 2006, 128, 1035810359;
  • 21m
    see also reference [15].
  • 22
    Meyer–Schuster isomerization of ethoxyalkynyl carbinols catalyzed by the vanadium(IV) derivative [V(O)(acac)2] has also been described: see reference[12].
  • 23
    J. Romero-Fernández, F. Carrillo-Hermosilla, A. Antiñolo, C. Alonso-Moreno, A. M. Rodríguez, I. López-Solera, A Otero, Dalton Trans. 2010, 39, 64196425.
  • 24
    N. Kamigata, T. Satoh, M. Yoshida, Bull. Chem. Soc. Jpn. 1988, 61, 449454.
  • 25
    See, for example:
  • 25a
    Microwaves in Organic Synthesis (Ed.: A. Loupy), Wiley-VCH, Weinheim, 2006;
  • 25b
    C. O. Kappe, D. Dallinger, S. S. Murphree in Practical Microwave Synthesis for Organic Chemists, Wiley-VCH, Weinheim, 2009;
  • 25c
    Microwave Heating as a Tool for Sustainable Chemistry (Ed.: N. E. Leadbeater), CRC Press, Boca Raton, 2011.
  • 26
    The use of lower temperatures and/or catalyst loadings slowed down the reaction considerably; as an example, by using 1 mol % of complex 2 under MW irradiation (300 W) at 80 °C, 3,3-diphenylpropenal was formed in only 80 % GC yield after 1 h.
  • 27
    This total Meyer–Schuster-versus-Rupe selectivity was also observed previously for the related vanadium(V) catalyst [V(O)(OSiPh3)3]: see reference [21g].
  • 28
    Such an E selectivity with secondary alkynols has been rarely observed using oxo complexes as catalysts: see reference [16a]. However, several examples of stereoselective non-oxo catalytic systems are known: see, for example, references [16b,c] and
  • 28a
    V. Cadierno, J. Francos, J. Gimeno, Tetrahedron Lett. 2009, 50, 47734776;
  • 28b
    V. Cadierno, S. E. García-Garrido, J. Gimeno, Adv. Synth. Catal. 2006, 348, 101110;
  • 28c
    J. García-Álvarez, J. Díez, J. Gimeno, C. M. Seifried, Chem. Commun. 2011, 47, 64706472.
  • 29
    For a recent review article and a book on the chemistry of these species, see:
  • 29a
    S. V. Druzhinin, E. S. Balenkova, V. G. Nenajdenko, Tetrahedron 2007, 63, 77537808;
  • 29b
    V. G. Nenajdenko, S. V. Druzhinin, E. S. Balenkova in Chemistry of α,β-Unsaturated Trifluoromethyl Ketones, Nova Science Publishers, New York, 2007.
  • 30
    These substrates can be easily accessed by the addition of CF3C[TRIPLE BOND]CLi, generated in situ from commercially available 2-bromo-3,3,3-trifluoropropene and lithium diisopropylamide, to the corresponding carbonyl compound. See, for example:
  • 30a
    A. R. Katritzky, M. Qi, A. P. Wells, J. Fluorine Chem. 1996, 80, 145147;
  • 30b
    N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume, S. Nakamura, J. Org. Chem. 1995, 60, 43634374;
  • 30c
    Y. Watanabe, T. Yamazaki, J. Fluorine Chem. 2010, 131, 646651.
  • 31
    Redox-type isomerizations, that is, isomerizations not involving a 1,3-shift of the hydroxyl moiety, of CF3-containing secondary propargylic alcohols into enones were described recently: Y. Watanabe, T. Yamazaki, J. Org. Chem. 2011, 76, 19571960.
  • 32
    Primary propargylic alcohols have been proven to be very difficult substrates for the Meyer–Schuster reaction. Only one successful methodology involving the combined use of cis-[MoO2(acac)2], [AuCl(PPh3)], and AgOTf has been described to date in the literature: see reference [19b].
  • 33
    M. M. Midland, J. Org. Chem. 1975, 40, 22502252.
  • 34
     
  • 34a
    J. Suffert, D. Toussaint, J. Org. Chem. 1995, 60, 35503553;
  • 34b
    B. D. Sherry, A. T. Radosevich, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 60766077.