Stereocontrolled asymmetric synthesis of optically active acylcyclopropane derivatives by Michael additions of bromomalonate to chiral α-acylvinylic sulfoxides

DOI: 10.1248/cpb.42.985

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 985 - 987 (1994)

Update date:2022-08-04

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Authors:

Hiroi Hiroi

Arinaga Arinaga

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Article abstract of DOI:10.1248/cpb.42.985

Michael addition of bromomalonate carbanions to chiral α-acylvinylic sulfoxides and the subsequent intramolecular alkylation yielded optically active acylcyclopropane derivatives with high enantiomeric excess. Stereochemistry of the product was determined by chemical correlation to a compound of known absolute configuration. The mechanism for the asymmetric induction is deduced on the basis of the stereochemical results obtained.

Full text of DOI:10.1248/cpb.42.985

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