Chiral Acetylenic Sulfoxide in Organic Synthesis: Addition of Chiral Secondary Amines

Sujun      Yan; K.   T.   Lam; K.   T.   Mo; W.   Y.   Wong; W.   H.   Chan; Albert   W.M.   Lee

doi:10.2174/1570178053400171

Abstract

Chiral secondary amines of the 3,4-dimethoxyphenylethyl and the tryptamine system were reacted with chiral acetylenic sulfoxides and achiral acetylenic sulfone. In the case of 3,4-dimethoxyphenylethyl amine, much improved diastereoselectivity (96 : 4) was observed as compared to the reaction of achiral secondary amine with chiral acetylenic sulfoxides.

Keywords: chiral sulfoxide, asymmetric synthesis, alkaloid synthesis, diastereoselectivity

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Letters in Organic Chemistry

Title: Chiral Acetylenic Sulfoxide in Organic Synthesis: Addition of Chiral Secondary Amines

Volume: 2 Issue: 1

Author(s): Sujun Yan, K. T. Lam, K. T. Mo, W. Y. Wong, W. H. Chan and Albert W.M. Lee

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Keywords: chiral sulfoxide, asymmetric synthesis, alkaloid synthesis, diastereoselectivity

Abstract: Chiral secondary amines of the 3,4-dimethoxyphenylethyl and the tryptamine system were reacted with chiral acetylenic sulfoxides and achiral acetylenic sulfone. In the case of 3,4-dimethoxyphenylethyl amine, much improved diastereoselectivity (96 : 4) was observed as compared to the reaction of achiral secondary amine with chiral acetylenic sulfoxides.

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Yan Sujun, Lam T. K., Mo T. K., Wong Y. W., Chan H. W. and Lee W.M. Albert, Chiral Acetylenic Sulfoxide in Organic Synthesis: Addition of Chiral Secondary Amines, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053400171