Organocatalytic enantioselective allylic alkylation of MBH carbonates with beta-keto esters

Abstract

The highly stereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with beta-ketoesters catalysed by beta-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantio-selectivity (up to 95% ee).

Keywords

• Baylis-Hillman carbonates
• quaternary stereogenic centers
• asymmetric phase-transfer
• stereoselective construction
• tertiary stereocenters
• adjacent quaternary
• kinetic resolution
• gamma-butenolides
• vicinal tertiary
• phosphine oxides