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Efficient Asymmetric Synthesis of Structurally Diverse P‐Stereogenic Phosphinamides for Catalyst Design
Author(s) -
Han Zhengxu S.,
Zhang Li,
Xu Yibo,
Sieber Joshua D.,
Marsini Maurice A.,
Li Zhibin,
Reeves Jonathan T.,
Fandrick Keith R.,
Patel Nitinchandra D.,
Desrosiers JeanNicolas,
Qu Bo,
Chen Anji,
Rudzinski DiAndra M.,
Samankumara Lalith P.,
Ma Shengli,
Grinberg Nelu,
Roschangar Frank,
Yee Nathan K.,
Wang Guijun,
Song Jinhua J.,
Senanayake Chris H.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500350
Subject(s) - stereocenter , enantioselective synthesis , combinatorial chemistry , nucleophile , catalysis , chemistry , phosphinate , lewis acids and bases , nucleophilic substitution , stereochemistry , organic chemistry , fire retardant
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.