Recent advances on asymmetric Strecker reactions

Xiao-Hua Cai,Bing Xie,Viktor V Zhdankin

doi:10.3998/ark.5550190.p008.487

Abstract

The Strecker reaction is one of the most attractive methods for the synthesis of �-amino acids and other bioactive compounds including natural products. The asymmetric Strecker reaction represents a simple and efficient method for the synthesis of optically pure �-amino acid derivatives, nucleic acids, various nitrogen and sulfur containing heterocycles and pharmaceuticals. Over the past several decades, considerable effort has been devoted towards the development of asymmetric Strecker reactions. This review provides an overview of recent asymmetric Strecker reactions, from diastereoselective reactions and catalytic enantioselective reactions including chiral catalytic metal systems and chiral organocatalytic systems.

Highlights

The Strecker reaction,[1] the oldest known synthesis of α-aminonitriles, is one of the most general methods, potentially useful for the syntheses of α-amino acids and other bioactive compounds including natural products
The imines react with CN– anion to give α-aminonitriles, which are subsequently hydrolyzed to the desired α-amino acid (Scheme 1)
Many chemists have taken an interest in the development of enantioselective, or catalytic asymmetric, reactions that use a catalyst to selectively increase the formation of a particular enantiomer

Summary

Introduction

The Strecker reaction,[1] the oldest known synthesis of α-aminonitriles, is one of the most general methods, potentially useful for the syntheses of α-amino acids and other bioactive compounds including natural products. The original Strecker synthesis can only produce a racemic mixture of the enantiomeric forms of an amino acid. For this reason, many chemists have taken an interest in the development of enantioselective, or catalytic asymmetric, reactions that use a catalyst to selectively increase the formation of a particular enantiomer. Asymmetric Strecker reactions using chiral aldehyde or ketone derived imines can be found in many natural product syntheses, this strategy tends to be extremely specific and highly structure-dependent. The following review will summarize recent achievements in asymmetric Strecker reaction from diastereoselective reactions and catalytic enantioselective reactions including chiral catalytic metal systems and chiral organocatalytic systems

Diastereoselective Strecker Reactions

Enantioselective Strecker Reaction Using Metal Catalysts

H R CN

Enantioselective Strecker Reactions using Organocatalysts

Findings

Conclusions