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Issue 42, 2016
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Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

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Abstract

We succeeded in the development of a new method for enantioselective synthesis of α-substituted-β-amino acid derivatives. Thus, nickel(0)-promoted carboxylation of ynamide gave the α-substituted-β-aminoacrylate derivative in a highly regioselective manner. Then, rhodium-catalyzed asymmetric hydrogenation of the α-substituted β-aminoacrylate produced the corresponding α-substituted β-amino acid derivative as an optically active form.

Graphical abstract: Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

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Publication details

The article was received on 07 Jun 2016, accepted on 01 Oct 2016, published on 04 Oct 2016 and first published online on 04 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01234E
Citation: Org. Biomol. Chem., 2016,14, 10080-10089
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    Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

    N. Saito, I. Abdullah, K. Hayashi, K. Hamada, M. Koyama and Y. Sato, Org. Biomol. Chem., 2016, 14, 10080
    DOI: 10.1039/C6OB01234E

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