Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines

Authors
Richards, EL Murphy, PJ Dinon, F Fratucello, S Brown, PM Gelbrich, T Hursthouse, MB
Citation
El. Richards et al., Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines, TETRAHEDRON, 57(36), 2001, pp. 7771-7784
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
36
Year of publication
2001
Pages
7771 - 7784
Database
ISI
SICI code
0040-4020(20010903)57:36<7771:ATSOTT>2.0.ZU;2-1
Abstract
The outcome of a tandem Michael/intramolecular aldol reaction which is medi ated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formatio n of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several ca ses but were still effective methods for the formation of 5-7 membered ring s. (C) 2001 Elsevier Science Ltd. All rights reserved.