Efficient Asymmetric Synthesis of P-Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents

被引：135

作者：

Han, Zhengxu S. ^{[1
]}

Goyal, Navneet ^{[1
]}

Herbage, Melissa A. ^{[1
]}

Sieber, Joshua D. ^{[1
]}

Qu, Bo ^{[1
]}

Xu, Yibo ^{[1
]}

Li, Zhibin ^{[1
]}

Reeves, Jonathan T. ^{[1
]}

Desrosiers, Jean-Nicolas ^{[1
]}

Ma, Shengli ^{[1
]}

Grinberg, Nelu ^{[1
]}

Lee, Heewon ^{[1
]}

Mangunuru, Hari P. R. ^{[1
]}

Zhang, Yongda ^{[1
]}

Krishnamurthy, Dhileep ^{[1
]}

Lu, Bruce Z. ^{[1
]}

Song, Jinhua J. ^{[1
]}

Wang, Guijun ^{[1
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 07期

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOGENIC PHOSPHORUS; KINETIC RESOLUTION; LIGANDS; DEPROTONATION; HYDROGENATION; BORANE; LIPASE; ROUTE;

D O I：

10.1021/ja312352p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 N and P-O 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.

引用

页码：2474 / 2477

页数：4

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