STEREOCONTROLLED ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ACYLCYCLOPROPANE DERIVATIVES BY MICHAEL ADDITIONS OF BROMOMALONATE TO CHIRAL ALPHA-ACYLVINYLIC SULFOXIDES

Authors
HIROI K ARINAGA Y
Citation
K. Hiroi et Y. Arinaga, STEREOCONTROLLED ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ACYLCYCLOPROPANE DERIVATIVES BY MICHAEL ADDITIONS OF BROMOMALONATE TO CHIRAL ALPHA-ACYLVINYLIC SULFOXIDES, Chemical and Pharmaceutical Bulletin, 42(4), 1994, pp. 985-987
Citations number
22
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
42
Issue
4
Year of publication
1994
Pages
985 - 987
Database
ISI
SICI code
0009-2363(1994)42:4<985:SAOOA>2.0.ZU;2-O
Abstract
Michael addition of bromomalonate carbanions to chiral alpha-acylvinyl ic sulfoxides and the subsequent intramoleculer alkylation yielded opt ically active acylcyclopropane derivatives with high enantiomeric exce ss. Stereochemistry of the product was determined by chemical correlat ion to a compound of known absolute configuration. The mechanism for t he asymmetric induction is deduced on the basis of the stereochemical results obtained.