Issue 12, 2021

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.

Graphical abstract: Access to P-stereogenic compounds via desymmetrizing enantioselective bromination

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Dec. 2020
Accepted
08 Febr. 2021
First published
12 Febr. 2021
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., 2021,12, 4582-4587

Access to P-stereogenic compounds via desymmetrizing enantioselective bromination

Q. Huang, Q. Zhou, C. Yang, L. Chen, J. Cheng and X. Li, Chem. Sci., 2021, 12, 4582 DOI: 10.1039/D0SC07008D

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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