1. Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design.
- Author
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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, Jean-Nicolas, Qu, Bo, Chen, Anji, Rudzinski, DiAndra M., Samankumara, Lalith P., Ma, Shengli, Grinberg, Nelu, Roschangar, Frank, Yee, Nathan K., Wang, Guijun, and Song, Jinhua J.
- Subjects
PHOSPHINE derivatives ,AMIDE derivatives ,ASYMMETRIC synthesis ,ENANTIOSELECTIVE catalysis ,PHOSPHINATES ,BENZOXAZINES ,LEWIS bases ,NUCLEOPHILIC substitution reactions - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2015
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