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Enantioselective Organocatalytic Synthesis of 1,2,3-Trisubstituted Cyclopentanes

Publication at Faculty of Science |
2021

Abstract

An organocatalytic asymmetric domino Michael/alpha-alkylation reaction between enals and non-stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1-bromo-3-nitropropane with alpha,beta-unsaturated aldehydes provides 1,2,3-trisubstituted cyclopentane carbaldehydes with high diastereo- (dr up to 8 : 1) and enantioselectivities (ee up to 96 %).