Cage-shaped borate esters with enhanced Lewis acidity and catalytic activity

被引：42

作者：

Yasuda, M

Yoshioka, S

Yamasaki, S

Somyo, T

Chiba, K

Baba, A

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Ryoka Syst Inc, Div Sci & Technol, Chuo Ku, Tokyo 1040033, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1021/ol053026+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cage shape causes high Lewis acidity and catalytic activity on boron. Borate esters that have cage-shaped ligands have accessible LUMO with lower eigenvalues than normal open-shaped borate esters. A large dihedral angle at C-O-B-O in cage-shaped borate esters induces less overlap between p-orbitals on O and B. The hetero-Diels-Alder reaction is effectively catalyzed by the cage-shaped borate, although the open-shaped borate does not act as a catalyst.

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页码：761 / 764

页数：4

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