Asymmetric synthesis of trans-disubstituted aryl-vinyl epoxides: a p-methoxy effect

Authors
Solladie-Cavallo, A Bouerat, L Roje, M
Citation
A. Solladie-cavallo et al., Asymmetric synthesis of trans-disubstituted aryl-vinyl epoxides: a p-methoxy effect, TETRAHEDR L, 41(38), 2000, pp. 7309-7312
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
38
Year of publication
2000
Pages
7309 - 7312
Database
ISI
SICI code
0040-4039(20000916)41:38<7309:ASOTAE>2.0.ZU;2-L
Abstract
It was found that trans-aryl-vinyl epoxides could be synthesized with 77-10 0% conversion from conjugated aldehydes (which could also behave as Michael accepters and lead to cyclopropanes) and chiral sulfonium salts with ee's ranging from 95 to 100%. When a p-methoxy group was present on the arylsulf onium salt, the epoxide was the sole product whatever The solvent. (C) 2000 Elsevier Science Ltd. All rights reserved.