cis- and enantio-selective cyclopropanation with chiral (ON+)Ru-salen complex as a catalyst

被引：93

作者：

Uchida, T ^{[1
]}

Irie, R ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ 33, Grad Sch Sci, Dept Mol Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 22期

关键词：

cyclopropanation; (salen)ruthenium; metallosalen; photoactivation;

D O I：

10.1016/S0040-4020(00)00273-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropanation of styrene with alpha-diazoacetate in the presence of (R,R)-(salen)ruthenium complex 4 in THF which dissolves the complex exhibits remarkable cis- and enantio-selectivity [cis:trans=97:3, >97% ee (1S,2R)], while the same reaction in hexane which does not dissolve it shows good but opposite sense of enantioselectivity [-83% ee (1R,2S)] together with moderate cis-selectivity (cis:trans=68:32). In homogeneous and heterogeneous conditions, (salen)ruthenium complexes are considered to have different ligand-conformation which, in turn, causes the opposite sense of enantioface selectivity in the cyclopropanation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3501 / 3509

页数：9

共 37 条

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