REVERSAL OF PI-FACE SELECTIVITY IN THE EVANS ALDOL REACTION WITH FLUORAL - A COMPUTATIONAL STUDY ON THE TRANSITION-STATES USING SEMIEMPIRICAL CALCULATIONS

Citation
Y. Makino et al., REVERSAL OF PI-FACE SELECTIVITY IN THE EVANS ALDOL REACTION WITH FLUORAL - A COMPUTATIONAL STUDY ON THE TRANSITION-STATES USING SEMIEMPIRICAL CALCULATIONS, Tetrahedron letters, 36(36), 1995, pp. 6527-6530
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
36
Issue
36
Year of publication
1995
Pages
6527 - 6530
Database
ISI
SICI code
0040-4039(1995)36:36<6527:ROPSIT>2.0.ZU;2-#
Abstract
Transition states for aldol reactions of boron enolate derived from N- acyloxazolidinone with acetaldehyde and fluoral were located by semiem pirical molecular orbital calculation. For reaction with acetaldehyde, a chair transition structure was found, while two open transition str uctures were obtained with fluoral. The transition states reproduced t he experimental results such that acetaldehyde and fluoral react prefe rentially on the re and si faces of the double bond of the boron enola te.