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One-Step Catalytic Enantioselective a-Quaternary 5-Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized a-Quaternary Proline Derivatives
Journal article   Peer reviewed

One-Step Catalytic Enantioselective a-Quaternary 5-Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized a-Quaternary Proline Derivatives

Palle Breistein, Jonas Johansson, Ismail Ibrahem, Shuangzheng Lin, Luca Deiana, Junliang Sun and Armando Cordova
Advanced synthesis & catalysis, Vol.354(6), pp.1156-1162
01/04/2012

Abstract

Chemistry Chemistry, Applied Chemistry, Organic Physical Sciences Science & Technology
The highly enantioselective cascade reaction between N-protected a-cyanoglycine esters and a,beta-unsaturated aldehydes is disclosed. The reaction represents a one-step entry to polysubstituted 5-hydroxyproline derivatives having a quaternary a-stereocenter generally in high yields with up to >95:5 dr and 99:1 er. It is also a direct catalytic two-step entry to functionalized a-quaternary proline derivatives.

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