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  • Diastereo- and enantioselective asymmetric hydrogenation of α-amido-β-keto phosphonates via dynamic kinetic resolution.

Diastereo- and enantioselective asymmetric hydrogenation of α-amido-β-keto phosphonates via dynamic kinetic resolution.

Organic letters (2012-12-25)
Xiaoming Tao, Wanfang Li, Xiaoming Li, Xiaomin Xie, Zhaoguo Zhang
ABSTRACT

Dynamic kinetic resolution of various α-amido-β-keto phosphonates via asymmetric hydrogenation proceeded efficiently to give the corresponding β-hydroxy-α-amido phosphonates in high diastereo- and enantioselectivities (up to 99:1 syn/anti, 99.8% ee). The addition of catalytic amounts of CeCl(3)·7H(2)O is necessary to achieve both good selectivity and catalytic efficiency under mild reaction conditions.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.9% trace metals basis
Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.999% trace metals basis
Sigma-Aldrich
Cerium(III) chloride heptahydrate, purum p.a., ≥98.0% (AT)
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, 99.9%
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, ≥99.99% trace metals basis