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Chem Asian J. 2013 Sep;8(9):2167-74. doi: 10.1002/asia.201300339. Epub 2013 Jun 17.

Highly efficient synthesis of heterocyclic and alicyclic β2-amino acid derivatives by catalytic asymmetric hydrogenation.

Author information

  • 1School of Chemistry and Chemical Engineering, Guangdong Engineering Research Center of Chiral Drugs, Sun Yat-sen University, No. 135 Xingangxi Road, Guangzhou 510275, People's Republic of China.

Abstract

A valuable class of new heterocyclic and alicyclic prochiral α-aminomethylacrylates has been conveniently synthesized through a three-step transformation involving a Baylis-Hillman reaction, O-acetylation, and a subsequent allylic amination. The corresponding novel β(2)-amino acid derivatives were prepared with excellent enantioselectivities and high yields by catalytic asymmetric hydrogenation using the catalyst rhodium(Et-Duphos) (Et-Duphos = 2',5',2'',5''-tetraethyl-1,2-bis(phospholanyl)benzene)) under mild reaction conditions (up to 99 % ee and S/C = 1000). The influence of the substrate on the enantioselectivity and reactivity is investigated, and the most suitable substrate configuration for the highly efficient enantioselective hydrogenation of β-substituted α-aminomethylacrylates under the Rh-Duphos system is reported. The current protocol provides a very practical, facile, and scalable method for the preparation of heterocyclic and alicyclic β(2)-amino acids and their derivatives.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

amino acids; asymmetric catalysis; heterocycles; hydrogenation; rhodium

PMID:
23776190
[PubMed - indexed for MEDLINE]
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