CHIRAL ARENETHIOLATOCOPPER(I) CATALYZED SUBSTITUTION-REACTIONS OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS

Authors
VANKLAVEREN M PERSSON ESM DELVILLAR A GROVE DM BACKVALL JE VANKOTEN G
Citation
M. Vanklaveren et al., CHIRAL ARENETHIOLATOCOPPER(I) CATALYZED SUBSTITUTION-REACTIONS OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS, Tetrahedron letters, 36(17), 1995, pp. 3059-3062
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
17
Year of publication
1995
Pages
3059 - 3062
Database
ISI
SICI code
0040-4039(1995)36:17<3059:CACSOA>2.0.ZU;2-B
Abstract
Asymmetric induction can be achieved in the gamma-selective substituti on reaction of allylic substrates (RCH=CH-CH2Y) with n-BuMgI catalyzed by the chiral arenethiolatocopper(I) complex 1b. It was found that th e enantiomeric excess of the gamma-substituted product (R'CH(n-Bu)CH=C H2) is influenced by the coordinating ability of the leaving group Y, and e.e.'s of up to 42% (R' = Cy, Y = OAc) have been obtained.