Abstract

The authors report an organocatalytic asymmetric Michael-aldol condensation reaction for the generation of chiral cyclopentenes. Diphenyl prolinol trimethyl silyl ether 1 in combination with sodium acetate was found to be the best catalyst system for this reaction. Without the additive the reaction yield was somewhat lower. With 10 mol% of catalyst 1, good yields (63-89%) and excellent enantioselectivities (er = 96:4 to 98:2) are obtained for different α,β-unsaturated aldehydes.

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