login

Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

Journal of the American Chemical SocietyPublished 1 June 2005
Douglas E. Fuerst, Eric N. Jacobsen
Citations322
SJR quartileQ1
SJR score5.55
SNIP2.61

TL;DR

The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones, suggesting a cooperative mechanism involving electrophile activation by thiOUrea and nucleophile activation by the amine.

Abstract

The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.

Keywords

Chemistry