THE HYDROXYPINANONE AS CHIRAL AUXILIARY IN MICHAEL ADDITIONS - AN INVERSION OF DIASTEREOSELECTIVITY AT LOW CONCENTRATION OF ENOLATE, A SUBSTRATE-DIRECTED APPROACH

Authors
SOLLADIECAVALLO A KOESSLER JL ISARNO T ROCHE D ANDRIAMIADANARIVO R
Citation
A. Solladiecavallo et al., THE HYDROXYPINANONE AS CHIRAL AUXILIARY IN MICHAEL ADDITIONS - AN INVERSION OF DIASTEREOSELECTIVITY AT LOW CONCENTRATION OF ENOLATE, A SUBSTRATE-DIRECTED APPROACH, Synlett, (2), 1997, pp. 217
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
2
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):2<217:THACAI>2.0.ZU;2-R
Abstract
Inversion of diastereoselectivity (from 90-98% S to 90-95% R) was obse rved for Michael additions as a function of the starting chiral enolat e concentration. It is also shown that catalytic amount of a phosphaze ne base (t-Oct-P2) allowed rapid reaction (1h), total conversion and h igh (90%) R-diastereoselectivity.