CONCERNING THE DIASTEREOFACIAL SELECTIVITY OF THE REACTION OF (E)-BETA-NITROENONES WITH KETONE ENOLATES

Authors
AHRACH M SCHNEIDER R GERARDIN P LOUBINOUX B
Citation
M. Ahrach et al., CONCERNING THE DIASTEREOFACIAL SELECTIVITY OF THE REACTION OF (E)-BETA-NITROENONES WITH KETONE ENOLATES, Tetrahedron, 54(50), 1998, pp. 15215-15226
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
50
Year of publication
1998
Pages
15215 - 15226
Database
ISI
SICI code
0040-4020(1998)54:50<15215:CTDSOT>2.0.ZU;2-5
Abstract
Stereoselectivity of the reaction of acyclic ketone enolates with (E)- beta-nitroenones was investigated according to the nature of the base used to accomplish deprotonation. The stereoselectivity and the regios electivity of the reaction of ketone enolates with (E-(beta)-nitroenon es could be enhanced by the use of trichlorotitanium enolates, which a llowed the formation of diastereomeric mixture of (E)-3-hydroxy-5-nicr oalk-4-enones 3 where the amount of product of (l) configuration is in creased compared to results obtained with lithium enolates. (C) 1998 E lsevier Science Ltd. All rights reserved.