Synthesis and catalytic epoxidation activity of terpene-derived D-4-symmetric metalloporphyrins

被引：20

作者：

Barry, JF ^{[1
]}

Campbell, L ^{[1
]}

Smith, DW ^{[1
]}

Kodadek, T ^{[1
]}

机构：

[1] UNIV TEXAS,DEPT CHEM & BIOCHEM,AUSTIN,TX 78712

来源：

TETRAHEDRON | 1997年 / 53卷 / 23期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(97)00470-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here a flexible synthesis of chiral, Dq-symmetric porphyrins from cyclic ketone starting materials. Two porphyrins have been synthesized from the terpene 1-R-(+)-nopinone, obviating the need to perform a resolution. The chloromanganese derivative of one of these porphyrins is a good catalyst for the epoxidation of terminal alkenes, providing epoxides with e.e.'s of 70% with high turnover numbers. A predictive model for oxygen atom transfer in the chiral pocket is discussed. (C) 1997 Elsevier Science Ltd.

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收藏

页码：7753 / 7776

页数：24

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