Topic
Strecker amino acid synthesis
About: Strecker amino acid synthesis is a research topic. Over the lifetime, 935 publications have been published within this topic receiving 24394 citations. The topic is also known as: Strecker reaction & Strecker synthesis.
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742 citations
TL;DR: This paper presents the chiral Titanium(IV) Complexes as a Catalyst for Strecker Reaction using Amines, Aldehydes, and HCN for transformation of R-Amino Nitriles into Amino Acid Amides.
Abstract: 3.1. Overview 2807 3.2. Chiral Aluminum(III) Complexes as a Catalyst 2808 3.2.1. Aluminum(III)-Salen-Based Catalysts 2808 3.2.2. Aluminum(III)-Binaphthol-Based Catalysts 2810 3.3. Chiral Titanium(IV) Complexes as a Catalyst 2814 3.3.1. Titanium(IV)-Peptide-Based Catalysts 2814 3.3.2. Titanium(IV)-Diol-Based Catalysts 2817 3.4. Chiral Zirconium(IV) Complexes as a Catalyst 2818 3.4.1. The Catalytic Concept 2818 3.4.2. The Substrate Range 2818 3.4.3. Strecker Reaction using Amines, Aldehydes, and HCN 2819 3.4.4. Transformation of R-Amino Nitriles into Amino Acid Amides 2820
520 citations
TL;DR: Rational optimization of catalyst structure based on the mechanistic insight led to an improved catalyst for the asymmetric Strecker reaction.
Abstract: A mechanistic investigation of the asymmetric Strecker reaction catalyzed by a metal-free Schiff base catalyst was conducted. The active site of the catalyst, the relevant stereoisomer of the imine substrate, and the solution structure of the imine−catalyst complex were elucidated using a series of kinetics, structure−activity, and NMR experiments. An unusual bridging interaction between the imine and the urea hydrogens of the catalyst was identified and supported by computation. Rational optimization of catalyst structure based on the mechanistic insight led to an improved catalyst for the asymmetric Strecker reaction.
492 citations
TL;DR: A review of α-amino nitriles can be found in this paper, where the authors highlight recent developments in the chemistry and applications of αamino n-nitriles.
Abstract: Bifunctional α-amino nitriles are not only versatile
intermediates in organic synthesis but also exhibit a valuable dual
reactivity, which has been utilized in a broad range of synthetic
applications. This review highlights recent developments in the chemistry
of α-amino nitriles, including asymmetric synthesis of α-amino
acids via Strecker reactions using chiral auxiliaries and
catalysts, α-amino nitriles as masked iminium ion equivalents in
cationic reactions and the synthesis of natural products and heterocycles,
and α-metallation to provide nucleophilic acyl anion equivalents and
applications to asymmetric Umpolung reactions.
451 citations
TL;DR: A novel catalytic enantioselective Strecker synthesis of chiral alpha-amino nitriles and alpha-AMino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity.
399 citations