Efficient Asymmetric Synthesis of Structurally Diverse P‐Stereogenic Phosphinamides for Catalyst Design |
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Authors: | Dr. Zhengxu S. Han Li Zhang Yibo Xu Dr. Joshua D. Sieber Dr. Maurice A. Marsini Dr. Zhibin Li Dr. Jonathan T. Reeves Dr. Keith R. Fandrick Nitinchandra D. Patel Dr. Jean‐Nicolas Desrosiers Dr. Bo Qu Anji Chen DiAndra M. Rudzinski Dr. Lalith P. Samankumara Dr. Shengli Ma Dr. Nelu Grinberg Dr. Frank Roschangar Dr. Nathan K. Yee Dr. Guijun Wang Dr. Jinhua J. Song Dr. Chris H. Senanayake |
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Affiliation: | 1. Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. 900 Ridgebury Road, Ridgefield, CT 06877 (USA);2. Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, VA 23529 (USA) |
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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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Keywords: | asymmetric catalysis chirality nucleophilic substitution organocatalyst phosphinamides |
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