STEREOSELECTIVE 1,4-ADDITION OF GRIGNARD-REAGENTS TO CHIRAL GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED KETONES

Authors
RACZKO J
Citation
J. Raczko, STEREOSELECTIVE 1,4-ADDITION OF GRIGNARD-REAGENTS TO CHIRAL GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED KETONES, Tetrahedron : asymmetry, 8(22), 1997, pp. 3821-3828
Citations number
43
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
22
Year of publication
1997
Pages
3821 - 3828
Database
ISI
SICI code
0957-4166(1997)8:22<3821:S1OGTC>2.0.ZU;2-8
Abstract
Copper-catalyzed conjugate addition reactions of Grignard reagents to gamma-alkoxy-alpha,beta-unsaturated ketones, derived from mandelic aci d, have been studied. Diastereoselectivity is strongly dependent on th e nature of the gamma-alkoxy protection group. Bulky silyl protection gives poor stereoselectivities, whereas the ketone bearing benzyloxyme thylene (BOM) protection reacts with excellent yields and stereoselect ivities. (C) 1997 Elsevier Science Ltd.