First synthesis of (-)-(1R,4R)- and (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)-methanol: new fenchone-derived chiral auxiliaries

Authors
Gosselin, P Lelievre, M Poissonnier, B
Citation
P. Gosselin et al., First synthesis of (-)-(1R,4R)- and (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)-methanol: new fenchone-derived chiral auxiliaries, TETRAHEDR-A, 12(15), 2001, pp. 2091-2093
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
15
Year of publication
2001
Pages
2091 - 2093
Database
ISI
SICI code
0957-4166(20010829)12:15<2091:FSO(A(>2.0.ZU;2-T
Abstract
The treatment of (+)- or (-)-fenchones epoxides with 1:2 85% H3PO4:DMSO for 30 min at 20 degreesC induced an enantiospecific Wagner-Meerwein rearrange ment affording new C(10)-O-substituted camphor derivatives which could prov e useful as chiral auxiliaries. (C) 2001 Elsevier Science Ltd. All rights r eserved.