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Access to P-stereogenic compounds via desymmetrizing enantioselective bromination.

ABSTRACT: A novel and efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported. Using this asymmetric ortho-bromination strategy, a wide range of chiral bisphenol phosphine oxides and bisphenol phosphinates were obtained with good to excellent yields (up to 92%) and enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction could be scaled up, and the synthetic utility of the desired P-stereogenic compounds was proved by transformations and application in an asymmetric reaction.

SUBMITTER: Huang QH

PROVIDER: S-EPMC8179578 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Access to P-stereogenic compounds via desymmetrizing enantioselective bromination.

Huang Qiu-Hong QH Zhou Qian-Yi QY Yang Chen C Chen Li L Cheng Jin-Pei JP Li Xin X

Chemical science 20210212 12

A novel and efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported. Using this asymmetric ortho-bromination strategy, a wide range of chiral bisphenol phosphine oxides and bisphenol phosphinates were obtained with good to excellent yields (up to 92%) and enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction could be scaled up, and the synthetic utility of the desired P-stereogenic ...[more]

PMID: 34163723

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