Synthesis of Highly Functionalized Proline Derivatives via a One-Pot Michael/S_N′-Addition/Cyclization Approach

Abstract

Chelated enolates undergo Michael addition towards halogenated α,β-unsaturated esters in a highly stereoselective fashion. The enolates formed can be trapped with electrophiles such as Baylis­-Hillman-type acrylates in a stereoselective fashion, before subsequent cyclization gives rise to substituted proline derivatives. Up to three stereogenic centers can be formed in this one-pot reaction.

Key words

amino acids - Baylis-Hillman - chelates - cyclization - Michael addition - one-pot reaction

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