A novel route to enantiopure cyclopentene carboxylic acids based on 3-endo-bromocamphor

Authors
Martinez, AG Vilar, ET Fraile, AG Cerero, SDM Maroto, BL
Citation
Ag. Martinez et al., A novel route to enantiopure cyclopentene carboxylic acids based on 3-endo-bromocamphor, TETRAHEDR-A, 12(2), 2001, pp. 189-191
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
2
Year of publication
2001
Pages
189 - 191
Database
ISI
SICI code
0957-4166(20010219)12:2<189:ANRTEC>2.0.ZU;2-M
Abstract
A novel four-step synthetic route to enantiopure cyclopentene carboxylic ac ids starting from commercially available 3-endo-bromocamphor is described. The synthesis is straightforward and practical. The key transformations inv olve firstly, an enantiospecific Wagner-Meerwein rearrangement of a bromoca mphor derived cyanohydrin, and secondly the regiospecific C-(1) C-(2) bond scission of a 7-bromonorbornan-3-one. (C) 2001 Elsevier Science Ltd. All ri ghts reserved.