Stereoselectivity in the Darzens condensation of substituted cyclohexanones with (-)-8-phenylmenthyl alpha-chloroacetate

Authors
Shinohara, Y Ohba, Y Takagi, R Kojima, S Ohkata, K
Citation
Y. Shinohara et al., Stereoselectivity in the Darzens condensation of substituted cyclohexanones with (-)-8-phenylmenthyl alpha-chloroacetate, HETEROCYCLE, 55(1), 2001, pp. 9-12
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
1
Year of publication
2001
Pages
9 - 12
Database
ISI
SICI code
0385-5414(20010101)55:1<9:SITDCO>2.0.ZU;2-S
Abstract
The Darzens condensation of 4-monosubstituted and cis-3,5-dimethyl-cyclohex anones with (-)-8-phenylmenthyl alpha -chloroacetate proceeded to give mixt ures of trans- and cis-glycidic esters with high enolate face selectivity ( >95% de). The presence of axial methyl substituents at the 3 and 5 position lead to decrease in enolate face selectivity. The configuration of the maj or products was determined by NMR, derivation, and/or X-Ray crystallographi c analysis.