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Synthesis 2015; 47(09): 1210-1226
DOI: 10.1055/s-0034-1380117
DOI: 10.1055/s-0034-1380117
short review
Catalytic Asymmetric Strecker Reaction: Bifunctional Chiral Tertiary Amine/Hydrogen-Bond Donor Catalysis Joins the Field
Further Information
Publication History
Received: 27 October 2014
Accepted after revision: 25 December 2014
Publication Date:
28 January 2015 (online)
Abstract
Bifunctional chiral tertiary amine/hydrogen-bond donor catalysis has recently emerged as a powerful strategy for developing catalytic asymmetric Strecker reactions for the synthesis of various types of optically active α-amino nitriles, useful as versatile building blocks for the synthesis of value-added products such as α-amino acids, 1,2-diamines, or heterocycles. This short review discusses the advantages of this strategy, summarizes recent advances, and describes the synthetic opportunities that remain open.
1 Introduction
2 Tertiary Amine/Hydrogen-Bond Donor Catalysis of Asymmetric Strecker Reactions
3 Summary and Outlook
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There are several other methods for preparing α�-amino acid derivatives. For asymmetric electrophilic amination reaction, see:
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For the direct functionalization of alcohols, see:
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For reviews, see:
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For the PyBox ligand 12, see:
For the P,N-1,1′-ferrocene ligand 14, see:
For the spiro phosphine oxazoline ligand 16, see:
For the chiral primary amine catalyst 24, see:
For reviews, see:
For reviews, see:
Such bifunctional catalysis was previously proposed for the cyanation of an aldehyde, see:
To the best of our knowledge, there are few reports on one-pot sequential catalytic asymmetric Strecker reactions; for successful examples based on aldehydes, see ref. 43b and:
For reviews on tertiary amine catalysis, see:
For reviews on hydrogen-bond donor catalysis, see:
For reviews on bifunctional tertiary amine/(thio)urea catalysis, see:
For pioneering work on cinchona alkaloid thiourea catalysts, see:
For reviews, see:
For examples of C–F/H–X interactions, see: