Efficient asymmetric synthesis of structurally diverse P-stereogenic phosphinamides for catalyst design

Angewandte Chemie
Zhengxu S HanChris H Senanayake

Abstract

The use of chiral phosphinamides is relatively unexplored because of the lack of a general method for the synthesis. Reported herein is the development of a general, efficient, and highly enantioselective method for the synthesis of structurally diverse P-stereogenic phosphinamides. The method relies on nucleophilic substitution of a chiral phosphinate derived from the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide. These chiral phosphinamides were utilized for the first synthesis of readily tunable P-stereogenic Lewis base organocatalysts, which were used successfully for highly enantioselective catalysis.

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Citations

Jun 11, 2016·Journal of the American Chemical Society·Zhijian HuangYonggui Robin Chi
May 10, 2017·Accounts of Chemical Research·Yan-Na MaShang-Dong Yang
Sep 16, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Miguel A del Águila-SánchezFernando López Ortiz
Apr 28, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Pau ClaveroMercè Font-Bardia
Aug 2, 2016·Chemical Society Reviews·Mathieu DutartreSylvain Jugé
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Jun 5, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Shangfei HuoWeiwei Zuo
Sep 11, 2020·Chemical Communications : Chem Comm·Cuiying WangChi-Ming Che
Jul 21, 2021·Journal of the American Chemical Society·Xu-Teng LiuQing-Wei Zhang
Sep 16, 2017·The Journal of Organic Chemistry·Masaharu SugiuraMakoto Nakajima
Oct 30, 2020·Journal of the American Chemical Society·Wenchao ChenChoon-Hong Tan
Oct 18, 2019·The Journal of Organic Chemistry·Xiaofeng WangQian Chen
Oct 8, 2019·Journal of the American Chemical Society·Xu-Teng LiuQing-Wei Zhang
Aug 24, 2019·Journal of the American Chemical Society·Barry M TrostChristopher A Kalnmals
Feb 28, 2020·Accounts of Chemical Research·Albert CabréXavier Verdaguer
Mar 5, 2020·The Journal of Organic Chemistry·Maria BioscaMontserrat Diéguez
Dec 23, 2020·Organic Letters·Bram B C PetersPher G Andersson
Oct 13, 2021·Organic Letters·Xiang Ren, Zhan Lu

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