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Asymmetric Sulfa-Michael Addition to α-Substituted Vinyl Ketones Catalyzed by Chiral Primary Amine

Niankai Fu, Long Zhang, Sanzhong Luo* and Jin-Pei Cheng

*Beijing National Laboratory for Molecule Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P.R. China, Email: luosziccas.ac.cn

N. Fu, L. Zhang, S. Luo, J.-P. Cheng, Org. Lett., 2014, 16, 4626-4629.

DOI: 10.1021/ol5022178


Abstract

Efficient, asymmetric conjugate addition-protonation reactions of thiols to α-substituted vinyl ketones are catalyzed by a chiral primary-tertiary diamine derived from l-phenylalanine. This organocatalyst promotes the sulfa-Michael addition-protonation reactions with good to excellent enantioselectivity.

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Key Words

Michael addition of thiols, organocatalysis


ID: J54-Y2014