Issue 15, 2019

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
05 12月 2018
Accepted
12 3月 2019
First published
12 3月 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 4322-4327

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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