Preparation of Enantiomerically Pure β??Silylcarboxyl Derivatives by Asymmetric 1, 4??Addition to N??Enoyl??sultams. Preliminary Communication

…, RJ Mills, W Pachinger, T Stevenson

Index: Oppolzer, Wolfgang; Mills, Robert J.; Pachinger, Werner; Stevenson, Thomas Helvetica Chimica Acta, 1986 ,  vol. 69, p. 1542 - 1545

Full Text: HTML

Citation Number: 87

Abstract

Abstract EtAlCl 2-promoted additions of organocopper reagents to camphor-derived, conjugated N-enoyl-sultams gave saturated and olefinic β-silylcarboxyl derivatives with high diastereodifferentiation. Nondestructive removal of the chiral auxiliary followed by oxidative Si-C bond cleavage furnished enantiomerically pure acetate-derived aldols and propionate- derived 'anti'-aldols (via silyl-directed α-methylation).