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Issue 15, 2019
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Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols

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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.

Graphical abstract: Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols

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Publication details

The article was received on 05 Dec 2018, accepted on 12 Mar 2019 and first published on 12 Mar 2019


Article type: Edge Article
DOI: 10.1039/C8SC05439H
Chem. Sci., 2019,10, 4322-4327
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    G. Yang, Y. Li, X. Li and J. Cheng, Chem. Sci., 2019, 10, 4322
    DOI: 10.1039/C8SC05439H

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