Abstract
The synthesis of a wide range of alkenyl 4,6- O-( S)-benzylidene-β- d-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part of our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out. High diastereomeric excesses (80–100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected. The β- d-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives.
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