STEREOCHEMISTRY OF ADDITION OF ALLYLIC GRIGNARD-REAGENTS TO ALPHA,BETA-ETHYLENIC KETONES

Authors
ZAIR T SANTELLIROUVIER C SANTELLI M
Citation
T. Zair et al., STEREOCHEMISTRY OF ADDITION OF ALLYLIC GRIGNARD-REAGENTS TO ALPHA,BETA-ETHYLENIC KETONES, Journal of organic chemistry, 58(10), 1993, pp. 2686-2693
Citations number
69
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
10
Year of publication
1993
Pages
2686 - 2693
Database
ISI
SICI code
0022-3263(1993)58:10<2686:SOAOAG>2.0.ZU;2-4
Abstract
The stereochemistry of the addition of allylic Grignard reagents, (mai nly crotylmagnesium chloride) to various conjugated enones has been in vestigated and a compact transition state is postulated. For s-cis-eno nes bearing no bulky substituents, a boat transition state, involving a trans-crotylmagnesium chloride, occurs leading to erythro-1,5-hexadi en-3-ols as the major or only product.