Camphor as a natural source of chirality in asymmetric synthesis

Abstract

The readily available enantiomers of bornane[10,2]sultam serve as efficient, versatile and practical chiral auxiliaries. A selection of highly)-face-selective reactions of their N-enoyl derivatives (Diels-Alder additions, dihydroxylations, 1,4-additions) as well as of their O-metalated N,O-ketene acetals (aldolizations, alkylations, brominations, “aminations”) are described. Applications to the syntheses of natural products and, particularly, of enantiomerically pure α-amino acids demonstrate their preparative potential. © 1990 De Gruyter