STEREOSELECTIVITY IN THE ADDITION OF ALUM INUM AND MAGNESIUM REAGENTSTO ((S)R)-2-P-TOLYLSULFINYLCYCLOHEXANONES

Authors
BUENO AB CARRENO MC RUANO JLG
Citation
Ab. Bueno et al., STEREOSELECTIVITY IN THE ADDITION OF ALUM INUM AND MAGNESIUM REAGENTSTO ((S)R)-2-P-TOLYLSULFINYLCYCLOHEXANONES, Anales de quimica, 90(7-8), 1994, pp. 442-451
Citations number
40
Categorie Soggetti
Chemistry
Journal title
Anales de quimica → ACNP
ISSN journal
11302283
Volume
90
Issue
7-8
Year of publication
1994
Pages
442 - 451
Database
ISI
SICI code
1130-2283(1994)90:7-8<442:SITAOA>2.0.ZU;2-I
Abstract
The results obtained in the reactions of ((S)R)-2-p-tolylsulfinyl cycl ohexanones with several aluminun and magnesium reagents reported. High diastereoselectivities are observed in the presence of ZnBr2 regardel ess of the metal and the nature of the organic residue added (alkyl, a ryl, vinyl or ethynyl). An efficient 1,3-asymmetric induction process controlled by the sulfoxide gives rise to tertiary alkylcarbinols with a defined configuration of the new stereogenic center.