A facile and practical preparation of P-chiral phosphine oxides

Ronghua Xu; Zhenhua Gao; Yiteng Yu; Yehua Tang; Duanshuai Tian; Tian Chen; Yibing Chen; Guangqing Xu; Enxue Shi; Wenjun Tang

doi:10.1039/D1CC00646K

A facile and practical preparation of P-chiral phosphine oxides†

Ronghua Xu,‡^a Zhenhua Gao,‡^b Yiteng Yu,^c Yehua Tang,^a Duanshuai Tian,^c Tian Chen,^c Yibing Chen,^a Guangqing Xu,*^c Enxue Shi*^b and Wenjun Tang

*^acd

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* Corresponding authors

^a School of Physical Science and Technology, ShanghaiTech University, Shanghai 200031, China
E-mail: tangwenjun@sioc.ac.cn

^b State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China
E-mail: exshi@sina.com

^c State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China
E-mail: xugq@sioc.ac.cn

^d School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou 310024, China

Abstract

A practical and cost-effective synthetic method of P-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during solvolysis has been addressed and well controlled by employing a suitable solvent, a low reaction temperature, and an appropriate reaction time.

This article is part of the themed collection: Chemical Communications HOT articles

Chemical Communications

A facile and practical preparation of P-chiral phosphine oxides†

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A facile and practical preparation of P-chiral phosphine oxides

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