Catalytic asymmetric aldol-type reaction using a chiral tin(II) Lewis acid

Shu Kobayashi, Hiromi Uchiro, Isamu Shiina, Teruaki Mukaiyama

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Abstract

Highly diastereo- and enantioselective aldol-type reactions of a silyl enol ether with aldehydes including aromatic, aliphatic, and α,β-unsaturated ones are performed in propionitrile (solvent) by the use of a catalytic amount of chiral tin(II) Lewis acid consisting of tin(II) triflate and a chiral diamine. The asymmetric environments created by the chiral catalysts in the enantioselective aldol reaction are discussed by employing five kinds of chiral diamines.

Original languageEnglish
Pages (from-to)1761-1772
Number of pages12
JournalTetrahedron
Volume49
Issue number9
DOIs
Publication statusPublished - 26 Feb 1993

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