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Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols.

ABSTRACT: A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita-Baylis-Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were generated with excellent to good yields (up to 99%) and high enantioselectivities (up to 98.5?:?1.5 e.r.). The reaction was further investigated by the linear free energy relationship (LFER) analysis. A possible transition state was proposed and furthered verified by theoretical calculations.

SUBMITTER: Yang GH 

PROVIDER: S-EPMC6499109 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols.

Yang Guo-Hui GH   Li Yao Y   Li Xin X   Cheng Jin-Pei JP  

Chemical science 20190312 15

A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita-Baylis-Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were generated with excellent to good yields (up to 99%) and high enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction was further investigated by the linear free energy relationship (LFER) analysis  ...[more]

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