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Issue 20, 2011
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Asymmetric synthesis of α,β-diamino acid derivates via Mannich-type reactions of a chiral Ni(II) complex of glycine with N-tosyl imines

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Abstract

A practical procedure composed of an asymmetric Mannich-type reaction between N-tosyl imine and a Ni(II) complex of glycine with (R)-o-[N-(N-benzylprolyl)amino]bezaophenone (BPB) as a chiral auxiliary catalyzed by Et3N in DMF to (R,2R,3S)-complexes, and decomposition of products with HCl to offer syn-(2R,3S)-α,β-diamino acids, was developed. Stereochemical mechanism of the Mannich reaction was proposed and supported by determining the absolute configuration of the product of the Mannich reaction relying on X-ray analysis. This two-step approach to amino acids was a general method and adapted to large-scale preparation.

Graphical abstract: Asymmetric synthesis of α,β-diamino acid derivates via Mannich-type reactions of a chiral Ni(ii) complex of glycine with N-tosyl imines

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Publication details

The article was received on 28 May 2011, accepted on 07 Jul 2011 and first published on 08 Jul 2011


Article type: Paper
DOI: 10.1039/C1OB05848G
Citation: Org. Biomol. Chem., 2011,9, 7144-7150
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    Asymmetric synthesis of α,β-diamino acid derivates via Mannich-type reactions of a chiral Ni(II) complex of glycine with N-tosyl imines

    G. Song, M. Jin, Z. Li and P. Ouyang, Org. Biomol. Chem., 2011, 9, 7144
    DOI: 10.1039/C1OB05848G

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