Palladium-mediated synthesis of novel meso-chiral porphyrins:: cobalt-catalyzed cyclopropanation

被引：44

作者：

Chen, Y ^{[1
]}

Gao, GY ^{[1
]}

Zhang, XP ^{[1
]}

机构：

[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 30期

关键词：

chiral porphyrins; cobalt porphyrins; cyclopropanation; palladium-catalyzed; cross-coupling; C-N bond formation; C-O bond formation;

D O I：

10.1016/j.tetlet.2005.05.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diaryiporphyrins with readily available chiral alcohols and amides via palladium-inediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：4965 / 4969

页数：5

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