122. Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition toN-Enoyl-sultams. Preliminary Communication
     Oppolzer, W.; Mills, R. J.; Pachinger, W.; Stevenson, T.
     Helv. Chim. Acta 1986, 69, 1542-1545

EtAlCl₂-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).

DOI : 10.1002/hlca.19860690703