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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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Supplementary files

Article information


Submitted
05 Dec 2018
Accepted
12 Mar 2019
First published
12 Mar 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4322-4327
Article type
Edge Article

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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