Stereoselective synthesis of phosphoranyl aryloxiranes through the addition of a nucleophilic stable carbene to aromatic aldehydes

被引：19

作者：

Illa, O

Gornitzka, H

Baceiredo, A

Bertrand, G

Branchadell, V

Ortuño, RM

机构：

[1] Univ Toulouse 3, Lab Heterochim Fondamentale & Appl, UMR 5069, F-31062 Toulouse 04, France

[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

[3] Univ Calif Riverside, Dept Chem, CNRS, UCR,Joint Res Chem Lab,UMR 2282, Riverside, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 20期

关键词：

D O I：

10.1021/jo0350460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [2+1] addition of the stable (phosphanyl)(silyl)carbene 1 to aromatic aldehydes affords phosphoranyl aryloxiranes, a new class of polyfunctional epoxides, in high yields and excellent diastereoselectivity. No reaction is observed for aldehydes bearing strongly electron-donating groups. Theoretical calculations show a good correlation between Gibbs activation energy and the electronic nature of the substituent on the phenyl ring.

引用

页码：7707 / 7710

页数：4

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