Kinetic Resolution of Racemic P-Chiral α-Hydroxymethylphos-phonates Catalyzed by Lipase from Porcine Pancreas

doi:10.6023/cjoc202212005

Abstract

The development of enzyme-catalyzed methods for the synthesis of P-chiral phosphine derivatives has important implications. Herein this work presents a direct biocatalytic transesterification of racemic α-hydroxyphosphonates and vinyl acetate, which provides a rapid access to P-chiral hydroxymethylphosphonates. Catalyzed by lipase from porcine pancreas (PPL), which is commercially available, the reactions proceed efficiently with a wide array of reaction partners to deliver various tertiary phosphine oxides in up to 49% yield and 83% ee under very mild conditions. The enzyme-substrate binding mode was established and the high enantioselectivity of PPL was revealed through docking simulations.

Key words: biocatalytic, kinetic resolution, hydroxymethylphosphonates, lipase from porcine pancreas

Cite this article

Huijuan Hu, Qiaoli Yan, Xiaogang Lu, Qifan Yang, Chengxin Pei, Hongmei Wang, Runli Gao. Kinetic Resolution of Racemic P-Chiral α-Hydroxymethylphos-phonates Catalyzed by Lipase from Porcine Pancreas[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2815-2825.

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