Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 2, Pages 1131-1135Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2020104
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A systematic study to evaluate the ability of various organocatalysts to catalyze the aldol reaction between acetone and 2,2,2-trifluoromethyl-l-phenylethanone was undertaken. Benchmark organocatalysts failed to catalyze this reaction. However, a prolinamide-thiourea consisting of (S)-prolinamide, (1S,2S)-diphenylethylenediamine, and (S)-ditert butyl aspartate proved to be an efficient catalyst, providing tertiary alcohols as the products of the reaction between ketones and perfluoroalkyl ketones in high to quantitative yields and high enantioselectivities (up 81% ee) at a catalyst loading of 2 mol %.
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