Cyclophane-Type Imidazolium Salts with Planar Chirality as a New Class of N-Heterocyclic Carbene Precursors

被引：43

作者：

Matsuoka, Yuki ^{[1
]}

Ishida, Yasuhiro ^{[1
]}

Sasaki, Daisuke ^{[1
]}

Saigo, Kazuhiko ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 30期

关键词：

carbenes; chirality; cyclophanes; heterocycles; umpolung;

D O I：

10.1002/chem.200800942

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclophane-type imidazolium salts with planar chirality were synthesized from enantiopure 2-amino alcohols, of which the N(1) and N(3) positions were connected with a bridge. The structural profiles of the imidazolium salts and their derivative N-heterocyclic carbenes (NHCs) were investigated by means of several analyses. The chiral NHCs derived from these imidazolium salts were found to catalyze the asymmetric cross-annulation of an a,p-unsaturated aldehyde with a ketone by means of the "conjugated" umpolung of the enal to give the target gamma-lactone with good to excellent enantioselectivity (up to 94% ee). Based on the expected structure of the NHCs and their intermediates, together with the absolute configuration of the products, a plausible mechanism for the stereocontrol was proposed.

引用

页码：9215 / 9222

页数：8

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