REVERSAL OF STEREOSELECTIVITY IN THE ALDOL REACTION OF BORON ENOLATE DERIVED FROM OPPOLZERS SULTAM WITH ALPHA,ALPHA-DIFLUORO AND ALPHA,ALPHA,ALPHA-TRIFLUORO CARBONYL-COMPOUNDS

Authors
ISEKI K OISHI S KOBAYASHI Y
Citation
K. Iseki et al., REVERSAL OF STEREOSELECTIVITY IN THE ALDOL REACTION OF BORON ENOLATE DERIVED FROM OPPOLZERS SULTAM WITH ALPHA,ALPHA-DIFLUORO AND ALPHA,ALPHA,ALPHA-TRIFLUORO CARBONYL-COMPOUNDS, Chemistry Letters, (6), 1994, pp. 1135-1138
Citations number
7
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
6
Year of publication
1994
Pages
1135 - 1138
Database
ISI
SICI code
0366-7022(1994):6<1135:ROSITA>2.0.ZU;2-Z
Abstract
Hexafluoroacetone causes the complete reversal of stereochemistry in t he aldol reaction of boron enolate derived from Oppolzer's sultam in t he absence of Lewis acids such as TiCl4. Trifluoroacetaldehyde and 2,2 -difluoro-5-phenyl-1-pentanal cause partial reversal, giving a mixture of syn- and anti-aldols, This finding was extended to reactions of th e boron enolate with phenylglyoxal and ethyl glyoxylate.