alpha-thiosubstituted chiral imines/secondary enamines: their use in the asymmetric Michael reaction

Authors
Nour, M Tan, K Cave, C Villeneuve, D Desmaele, D d'Angelo, J Riche, C
Citation
M. Nour et al., alpha-thiosubstituted chiral imines/secondary enamines: their use in the asymmetric Michael reaction, TETRAHEDR-A, 11(4), 2000, pp. 995-1002
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
4
Year of publication
2000
Pages
995 - 1002
Database
ISI
SICI code
0957-4166(20000310)11:4<995:ACIETU>2.0.ZU;2-M
Abstract
The asymmetric Michael reaction between 2-thiosubstituted chiral imines/sec ondary enamines derived from (S)I-phenylethylamine and electrophilic alkene s (methyl acrylate, MVK) was investigated. 2-Phenylthio derivatives furnish ed the expected Michael adducts with excellent ee. By contrast, an in situ elimination of p-toluenesulfenic acid took place when using the p-toluenesu lfinyl analogs. (C) 2000 Elsevier Science Ltd. All rights reserved.