A new convenient procedure for the preparation of enantiopure C10-S- and C10-Se-substituted camphor-derived sulfides and selenides

Authors
Martinez, AG Vilar, ET Fraile, AG Cerero, SD Maroto, BL
Citation
Ag. Martinez et al., A new convenient procedure for the preparation of enantiopure C10-S- and C10-Se-substituted camphor-derived sulfides and selenides, TETRAHEDR L, 42(30), 2001, pp. 5017-5019
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
30
Year of publication
2001
Pages
5017 - 5019
Database
ISI
SICI code
0040-4039(20010723)42:30<5017:ANCPFT>2.0.ZU;2-F
Abstract
The enantiospecific preparation of two novel C10-S(II)- and C10-Se(II)-subs tituted camphor derivatives (arylsulfide and arylselenide) from readily ava ilable camphor is described. The established three-step route constitutes a model procedure for the straightforward preparation of interesting enantio pure C10-S- and C10-Se-substituted camphor-derived chiral sources. The key- step of the described route is an enantiospecific Wagner-Meerwein rearrange ment of 3,3-dimethyl-2-methylenenorbornan-1-ol 6 under electrophilic treatm ent with an arylsulfenyl (or arylselenyl) chloride. (C) 2001 Elsevier Scien ce Ltd. All rights reserved.