EFFICIENT ASYMMETRIC-SYNTHESIS OF CIS-2-METHYLCYCLOPROPANECARBOXYLIC ACID

Authors
ONODA T SHIRAI R KAWAI N IWASAKI S
Citation
T. Onoda et al., EFFICIENT ASYMMETRIC-SYNTHESIS OF CIS-2-METHYLCYCLOPROPANECARBOXYLIC ACID, Tetrahedron, 52(42), 1996, pp. 13327-13338
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
42
Year of publication
1996
Pages
13327 - 13338
Database
ISI
SICI code
0040-4020(1996)52:42<13327:EAOCA>2.0.ZU;2-C
Abstract
We have developed a versatile method for the synthesis of enantiomeric ally pure cis-2-methylcyclopropanecarboxylic acid (-)-2, a component o f curacin A, and its enantiomer, (+)-2. Double-asymmetric Simmons-Smit h cyclopropanation of the dienes 5 and 9 derived from diethyl L-tartra te proceeded with excellent diastereofacial selectivity (>99% de) to g ive the dicyclopropanes 6 and 10, which were converted to both enantio mers of 2. Copyright (C) 1996 Published by Elsevier Science Ltd