Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement

被引：379

作者：

Shi, XD ^{[1
]}

Gorin, DJ ^{[1
]}

Toste, FD ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 16期

关键词：

D O I：

10.1021/ja051689g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rearrangement of 1-ethynyl-2-propenyl pivaloates to cyclopentenones catalyzed by cationic triphenylphosphinegold(I) complexes is described. The reaction tolerates both alkyl and aryl substitution at the acetylenic and olefinic positions. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched propargyl pivaloates proceeds with excellent chirality transfer, thus providing a practical method for the enantioselective synthesis of cyclopentenones. Copyright © 2005 American Chemical Society.

引用

页码：5802 / 5803

页数：2

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