Stereoselective Synthesis of P-Stereogenic Aminophosphines: Ring Opening of Bulky Oxazaphospholidines

被引：90

作者：

Leon, Thierry

Riera, Antoni ^{[1
]}

Verdaguer, Xavier

机构：

[1] Univ Barcelona, Unitat Recerca Sintesi Asimetr URSA PCB, Inst Res Biomed IRB Barcelona, E-08028 Barcelona, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

关键词：

ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; PHOSPHINE OXIDES; PHOSPHORUS; HYDROGENATION; LIGANDS; DIPHOSPHINES; INVERSION;

D O I：

10.1021/ja200988c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereoselective and efficient synthesis of P-stereogenic bulky alkyl and aryl aminophosphines that relies on ring opening of tert-butyl-oxazaphospholidine 2 is described. Ring opening with several organometallic reagents takes place with inversion of configuration at the phosphorus center as it has been demonstrated by X-ray analysis of two ring-opened intermediates. The unprecedented reactivity observed is attributed to the presence of a free NH functionality that facilitates the attack of the organometallic reagent in an S(N)2@P-type process.

引用

页码：5740 / 5743

页数：4

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