Efficient Asymmetric Synthesis of P-Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents
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- 作者：Zhengxu S. Han ; Navneet Goyal ; Melissa A. Herbage ; Joshua D. Sieber ; Bo Qu ; Yibo Xu ; Zhibin ; Li ; Jonathan T. Reeves ; Jean-Nicolas Desrosiers ; Shengli Ma ; Nelu Grinberg ; Heewon Lee ; Hari P. R. Mangunuru ; Yongda Zhang ; Dhileep Krishnamurthy ; Bruce Z. Lu ; Jinhua J. Song ; Guijun Wang ; Chris H. Senanayake
- 刊名：The Journal of the American Chemical Society
- 出版年：2013
- 出版时间：February 20, 2013
- 年：2013
- 卷：135
- 期：7
- 页码：2474-2477
- 全文大小：336K
- 年卷期：v.135,no.7(February 20, 2013)
- ISSN：1520-5126
文摘
A general, efficient, and highly diastereoselective method for the synthesis of structurally and sterically diverse P-chiral phosphine oxides was developed. The method relies on sequential nucleophilic substitution on the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide, which features enhanced and differentiated P鈥揘 and P鈥揙 bond reactivity toward nucleophiles. The reactivities of both bonds are fine-tuned to allow cleavage to occur even with sterically hindered nucleophiles under mild conditions.