CHIRAL DIENOLATE-BASED REMOTE ASYMMETRIC INDUCTION - THE ASYMMETRIC ALPHA-OXYLATION PD(0)-CATALYZED ALLYLIC SUBSTITUTION SEQUENCE LEADING TO GAMMA-CHIRAL ALPHA,BETA-UNSATURATED ACID-DERIVATIVES

Authors
SUGIURA M YAGI Y WEI SY NAKAI T
Citation
M. Sugiura et al., CHIRAL DIENOLATE-BASED REMOTE ASYMMETRIC INDUCTION - THE ASYMMETRIC ALPHA-OXYLATION PD(0)-CATALYZED ALLYLIC SUBSTITUTION SEQUENCE LEADING TO GAMMA-CHIRAL ALPHA,BETA-UNSATURATED ACID-DERIVATIVES, Tetrahedron letters, 39(24), 1998, pp. 4351-4354
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
24
Year of publication
1998
Pages
4351 - 4354
Database
ISI
SICI code
0040-4039(1998)39:24<4351:CDRAI->2.0.ZU;2-4
Abstract
The asymmetric alpha-oxylation of the dienolates derived from chiral a lpha,beta- or beta,gamma-unsaturated imide with dibenzyl peroxydicarbo nate followed by the Pd(0)-catalyzed reactions of the resulting allyli c carbonate with various nucleophiles (alkylation, etherification, and amination) is shown to provide the gamma-(S)- or -(R)configurated alp ha,beta-unsaturated imide, respectively, with a high level of stereoco ntrol. (C) 1998 Elsevier Science Ltd. All right reserved.