Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6 - Rare earth metal triflate complexes

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2989-2996

  Hamada, Tomoaki ^a   Manabe, Kei ^a   Ishikawa, Shunpei ^a   Nagayama, Satoshi ^a   Shiro, Motoo ^b   Kobayashi, Sho ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BINDING ENERGY; CATALYSIS; MOLECULAR STRUCTURE; POSITIVE IONS;

ADDUCTS;

COMPLEXATION;

ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; CROWN ETHER DERIVATIVE; KETONE DERIVATIVE; LANTHANIDE; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; THIOESTER; TRIFLUOROMETHANESULFONIC ACID;

ALDOL REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY;

EID: 0037433497     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028698z     Document Type: Article

References (52)

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3. For reviews on asymmetric aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. 3, p 998. (c) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (d) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (e) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
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34. For preparation of crown ethers 1, 3-7, see the Supporting Information.
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36. 3-catalyzed aldol reactions, see: ref 4b.
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39. Size effects of rare earth metals on enantioselectivity have been observed in asymmetric reactions. For example: (a) Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657. (b) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115. 9800. (c) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (d) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
40. Size effects of rare earth metals on enantioselectivity have been observed in asymmetric reactions. For example: (a) Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657. (b) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115. 9800. (c) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (d) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
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42. a values of pyridine, 4-methoxypyridine, and 4-bromopyridine in water at 25 °C are 5.17, 6.47, and 3.71, respectively. Lange's Handbook of Chemistry; Dean, J. A., Lange, N. A., Eds.; McGraw-Hill Book Company: New York, 1972; Section 5.
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51. The absolute configuration was determined to be 2R,3R after converting to the methyl ester. (a) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754. (b) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292.
52. The absolute configuration was determined to be 2R,3R after converting to the methyl ester. (a) Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754. (b) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292.