Organic Letters
Organic Letters
5 years ago

Nickel-Catalyzed Enantioselective Hydrogenation of β-(Acylamino)acrylates: Synthesis of Chiral β-Amino Acid Derivatives

Nickel-Catalyzed Enantioselective Hydrogenation of β-(Acylamino)acrylates: Synthesis of Chiral β-Amino Acid Derivatives
Xiuxiu Li, Xumu Zhang, Hui Lv, Shuailong Li, Cai You
The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95–99% yield) and enantioselectivities (97–99% ee). With the Ni–Binapine system, high enantioselectivities (98–99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02417

DOI: 10.1021/acs.orglett.7b02417

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