Diastereoselective Synthesis of Bulky, Strongly Nucleophilic, and Configurationally Stable P-Stereogenic Tricyclic Phosphines

被引：16

作者：

Gau, David ^{[1
]}

Rodriguez, Ricardo ^{[1
]}

Kato, Tsuyoshi ^{[1
]}

Saffon-Merceron, Nathalie ^{[2
]}

Baceiredo, Antoine ^{[1
]}

机构：

[1] Univ Toulouse, UPS, LHFA, F-31062 Toulouse, France

[2] CNRS, LHFA UMR 5069, F-31062 Toulouse, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 37期

关键词：

HETEROCYCLIC CARBENE LIGANDS; PHOSPHONIUM SILA-YLIDE; ENANTIOSELECTIVE HYDROGENATION; REACTIVITY; COMPLEXES; CATALYSIS; SILYLENE;

D O I：

10.1021/ja1054912

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A very simple, one-step highly diastereoselective synthesis of bulky, configurationally and air-stable P-chiral tricyclic phosphines 3, showing an exceptionally strong nucleophilic character, has been developed. This method involves the reaction of the stable phosphonium sila-ylide 1 with aryl- and alkyl-substituted acetylene derivatives. Starting from commercially available chiral (R,S)-(+)-endo-2-norborneol, the corresponding enantiomerically pure phosphines were obtained with excellent enantioselectivities (ee >= 99%) and high chemical yields.

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页码：12841 / 12843

页数：3

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