Access to P-stereogenic compounds via desymmetrizing enantioselective bromination.

Qiu-Hong Huang,Qian-Yi Zhou,Xin Li,Jin-Pei Cheng,Li Chen,Chen Yang

doi:10.1039/d0sc07008d

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.

Highlights

Qiu-Hong Huang,a Qian-Yi Zhou,a Chen Yang, a Li Chen, a Jin-Pei Chengab and Xin Li *a
A novel and efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported
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

Summary

Introduction

Qiu-Hong Huang,a Qian-Yi Zhou,a Chen Yang, a Li Chen, a Jin-Pei Chengab and Xin Li *a. A novel and efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported.

Results

Conclusion