Reactions of 1,2-cyclopropyl carbohydrates

Abstract

Addition of a carbene to a glycal is the prominent method for the synthesis of 1,2-cyclopropyl carbohydrates. This incorporation of a cyclopropane into a carbohydrate scaffold enables divergent reactivity, with the two main classes being ring expansion and cleavage to 2-C-branched carbohydrates. A wide variety of products are obtained depending on the functionality attached to the cyclopropane (none or ester or halogens) and the promoter (Lewis acid, Bronsted acid, halophile or base) used in the reaction. This article reviews progress in the synthesis and reactions of 1,2-cyclopropyl carbohydrates since 2000 and discloses efforts by our group in the area.