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Synfacts 2007(12): 1311-1311
DOI: 10.1055/s-2007-991337
DOI: 10.1055/s-2007-991337
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Direct Aldol-Type Reaction of Oxindoles with Ethyl Trifluoropyruvate
S. Ogawa, N. Shibata*, J. Inagaki, T. Toru*, S. Nakamura, M. Shiro
Nagoya Institute of Technology and Rigaku Corporation, tokyo, Japan
Further Information
Publication History
Publication Date:
22 November 2007 (online)
Significance
The authors report an organocatalytic asymmetric direct aldol reaction of oxindoles with ethyl 3,3,3-trifluoropyruvate. Cinchona alkaloid catalyst (DHQD)2PHAL (1) was found to be effective for this reaction. Its pseudoenantiomer (DHQ)2PHAL (2) gave the opposite enantiomer of the trifluoromethylated oxindole product. With 10 mol% of catalyst 1 or 2, good to high diastereoselectivities (dr = 71:29 to 97:3) and excellent enantioselectivities (er = 90:10 to >99:1) are obtained for different substituted oxindoles.