STEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO THE CARBONYL GROUP OF METHYL 1,4,5-TRIS(TRIMETHYLSILYL)-3-DEHYDROQUINATE

Authors
DESPEYROUX P BALTAS M GORRICHON L
Citation
P. Despeyroux et al., STEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO THE CARBONYL GROUP OF METHYL 1,4,5-TRIS(TRIMETHYLSILYL)-3-DEHYDROQUINATE, Bulletin de la Societe chimique de France, 134(8-9), 1997, pp. 777-784
Citations number
36
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
134
Issue
8-9
Year of publication
1997
Pages
777 - 784
Database
ISI
SICI code
0037-8968(1997)134:8-9<777:SINATT>2.0.ZU;2-X
Abstract
Methyl 1,4,5-tris(trimethylsilyl)-3-dehydroquinate was synthesized in a three-step procedure and condensed with various nucleophiles (-CH2CO OEt, -CH2SO2Ph, -CH2-C=CH, H-). The diastereoselectivity of the reacti on, leading to the creation of a new quaternary (or tertiary) asymmetr ic carbon atom aas examined. The preferential axial attack on the C=O group of the cyclohexanone system is discussed. The deprotected produc ts were evaluated as DHQase inhibitors.