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Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution.

ABSTRACT: The synthesis of P-stereogenic building blocks is extremely difficult. Herein we report an efficient kinetic resolution of secondary phosphine oxides via a Le-Phos-catalyzed asymmetric allylation reaction with Morita-Baylis-Hillman carbonates. This method provides facile access to enantioenriched secondary and tertiary P-chiral phosphine oxides with broad substrate scope, both of which could serve as P-stereogenic synthons, and can be rapidly incorporated into a given scaffold bearing a P-stereocenter. The highly desirable late stage modifications demonstrate the practicability of our method and can be a critical contribution to obtaining optimal P-chiral catalysts and ligands.

SUBMITTER: Qiu H

PROVIDER: S-EPMC8162192 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution.

Qiu Haile H Dai Qiang Q He Jiafeng J Li Wenbo W Zhang Junliang J

Chemical science 20200902 36

The synthesis of P-stereogenic building blocks is extremely difficult. Herein we report an efficient kinetic resolution of secondary phosphine oxides via a Le-Phos-catalyzed asymmetric allylation reaction with Morita-Baylis-Hillman carbonates. This method provides facile access to enantioenriched secondary and tertiary P-chiral phosphine oxides with broad substrate scope, both of which could serve as P-stereogenic synthons, and can be rapidly incorporated into a given ...[more]

PMID: 34094261

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