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
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.