Abstract
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.
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