Stereoselective azide introduction during 1,2-sulfur migration in alpha-hydroxyalkyldithioacetals

Authors
Afonso, CAM Barros, MT Maycock, CD
Citation
Cam. Afonso et al., Stereoselective azide introduction during 1,2-sulfur migration in alpha-hydroxyalkyldithioacetals, TETRAHEDRON, 55(3), 1999, pp. 801-814
Citations number
41
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
3
Year of publication
1999
Pages
801 - 814
Database
ISI
SICI code
0040-4020(19990115)55:3<801:SAID1M>2.0.ZU;2-5
Abstract
A series alpha-hydroxyalkyldithiolanes were reacted with a mixture of triph enylphosphine, diethyl azodicarboxylate and hydrazoic acid to give 2-azido- 1,4-dithianes stereoselectively. Reduction of the azido group to an amine r esulted in racemisation. (C) 1998 Elsevier Science Ltd. All rights reserved .