Recent Advances on <i>O</i>-Ethoxycarbonyl and <i>O</i>-Acyl Protected Cyanohydrins

Abstract

Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O-acyl protected cyanohydrins. Reactions using KCN or alkyl cyanoformates as the cyanide ion source are described, as well as organic and transition metal catalysis used in their preparation, including asymmetric cyanation. In a second part, transformations, and synthetic applications of O-ethoxycarbonyl/acyl cyanohydrins are presented. A variety of structures has been obtained starting from such protected cyanohydrins and, in particular, the synthesis of oxazoles, 1,4-diketones, 1,3-diketones, 2-vinyl-2-cyclopentenones through various methods are discussed.

Keywords

• <i>O</i>-protected cyanohydrins
• <i>O</i>-acyl cyanohydrins
• <i>O</i>-ethoxycarbonyl cyanohydrins
• cyanohydrin preparation
• catalysis
• ethylcyanocarbonates