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Asymmetric Catalysis with Bis(hydroxyphenyl)diamides/Rare-Earth Metal Complexes

Dr. Naoya Kumagai^*,
Prof. Dr. Masakatsu Shibasaki^*

Article first published online: 23 NOV 2012

DOI: 10.1002/anie.201206582

Issue

Angewandte Chemie International Edition

Volume 52, Issue 1, pages 223–234, January 2, 2013

Additional Information

How to Cite

Kumagai, N. and Shibasaki, M. (2013), Asymmetric Catalysis with Bis(hydroxyphenyl)diamides/Rare-Earth Metal Complexes. Angew. Chem. Int. Ed., 52: 223–234. doi: 10.1002/anie.201206582

Author Information

Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan) http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index_e.html

Email: Dr. Naoya Kumagai (nkumagai@bikaken.or.jp), Prof. Dr. Masakatsu Shibasaki (mshibasa@bikaken.or.jp)

^*Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan) http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index_e.html

Publication History

Issue published online: 20 DEC 2012
Article first published online: 23 NOV 2012
Manuscript Received: 15 AUG 2012

Funded by

MEXT KAKENHI. Grant Number: 15002003, 20200053
JSPS KAKENHI. Grant Number: 20229001, 19790008

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S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701.
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For selected examples of catalytic asymmetric conjugate addition of α-substituted α-cyanocalbonyl pronucleophiles for the formation of quaternary stereogenic centers, see:
39a
M. Sawamura, H. Hamashima, Y. Ito, J. Am. Chem. Soc. 1992, 114, 8295;
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M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 1313;
39d
H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948;
39e
K. Takenaka, M. Minakawa, Y. Uozumi, J. Am. Chem. Soc. 2005, 127, 12273;
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39g
B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768;
39h
X. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038;
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Recent reviews on direct Mannich reactions using unmodified pronucleophiles:
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M. Shibasaki, S. Matsunaga, J. Organomet. Chem. 2006, 691, 2089;
41b
A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797; general reviews on catalytic asymmetric Mannich reactions:
Direct Link:
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G. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541;
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For selected examples of catalytic asymmetric Mannich reactions with 1,3-dicarbonyl compounds generating quaternary stereocenters, see:
42a
M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359;
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A. L. Tillman, J. Ye, D. J. Dixon, Chem. Commun. 2006, 1191;
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M. Hatano, T. Maki, K. Moriyama, M. Arinobe, K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858;
42h
M. Hatano, T. Horibe, K. Ishihara, Org. Lett. 2010, 12, 3502; for selected examples of catalytic asymmetric Mannich reactions with 1,3-dicarbonyl compounds generating tertiary stereocenters, see:
42i
D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
42j
S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11256;
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J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048;
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N. Sasamoto, C. Dubs, Y. Hamashima, M. Sodeoka, J. Am. Chem. Soc. 2006, 128, 14010;
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T. Poisson, T. Tsubogo, Y. Yamashita, S. Kobayashi, J. Org. Chem. 2010, 75, 963.
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A. Nojiri, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 5630.
44
The reaction rate is accelerated in the presence of (S)-1 a, suggesting that hydrogen bonding promotes the reaction and enhances the stereodiscrimination at the transition state. For hydrogen bonding in peptide-based catalysts, see:
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G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 2001, 123, 6496;
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B. R. Sculimbrene, A. J. Morgan, S. J. Miller, J. Am. Chem. Soc. 2002, 124, 11653;
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M. Shibasaki, H. Gröger in Comprehensive Asymmetric Catalysis, Vol. III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1075–1090;
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F. A. Luzzio, Tetrahedron 2001, 57, 915;
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C. Palomo, M. Oiarbide, A. Mielgo, Angew. Chem. 2004, 116, 5558;
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53d
M. Shibasaki, H. Gröger, M. Kanai in Comprehensive Asymmetric Catalysis, Suppl. 1 (E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Hidelberg, 2004, pp. 131–133;
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J. Boruwa, N. Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315;
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C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. 2007, 2561;
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S. E. Milner, T. S. Moody, A. R. Maguire, Eur. J. Org. Chem. 2012, 3059.
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Selected examples of syn-selective catalytic asymmetric nitroaldol reactions:
54a
H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388;
54b
Y. Sohtome, Y. Hashimoto, K. Nagasawa, Eur. J. Org. Chem. 2006, 2894;
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Y. Sohtome, N. Takemura, K. Takada, R. Takagi, T. Iguchi, K. Nagasawa, Chem. Asian J. 2007, 2, 1150;
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T. Arai, R. Takashita, Y. Endo, M. Watanabe, A. Yanagisawa, J. Org. Chem. 2008, 73, 4903; for partially successful examples of syn-selective catalytic asymmetric nitroaldol reaction, see:
54f
J. Yoshimoto, C. A. Sandoval, S. Saito, Chem. Lett. 2008, 37, 1294;
54g
H. Y. Kim, K. Oh, Org. Lett. 2009, 11, 5682.
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56
For other examples of anti-selective catalytic asymmetric nitroaldol reactions, see:
56a
S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 3274;
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K. Lang, J. Park, S. Hong, Angew. Chem. 2012, 124, 1652;
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For partially successful examples of anti-selective catalytic asymmetric nitroaldol reactions, see:
57a
G. Blay, L. R. Domingo, V. Hernández-Olmos, J. R. Pedro, Chem. Eur. J. 2008, 14, 4725;
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57b
H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 2009, 19, 3895;
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A. Noole, K. Lippur, A. Metsala, M. Lopp, T. Kanger, J. Org. Chem. 2010, 75, 1313;
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57e
T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, H. Griengl, Angew. Chem. 2006, 118, 3532;
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M. Gruber-Khadjawi, T. Purkarthofer, W. Skranc, H. Griengl, Adv. Synth. Catal. 2007, 349, 1445.
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T. Sawaki, Y. Aoyama, J. Am. Chem. Soc. 1999, 121, 4793;
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B. Westermann, Angew. Chem. 2003, 115, 161;
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Angew. Chem. Int. Ed. 2003, 42, 151;
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K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843;
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T. P. Yoon, E. N. Jacobsen, Angew. Chem. 2005, 117, 470;
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Asymmetric Catalysis with Bis(hydroxyphenyl)diamides/Rare-Earth Metal Complexes

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