Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans

被引：137

作者：

Bowman, RK ^{[1
]}

Johnson, JS ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1021/ol052700k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild Ni(0)-catalyzed rearrangements of 1-acyl-2-vinylcyclopropanes have been developed. The room-temperature isomerizations afford dihydrofuran products in yields regularly greater than 90%. A highly substituted, stereochemically defined cyclopropane was employed in the rearrangement to evaluate the reaction mechanism. Product analysis indicates that the overall reaction proceeds with retention of configuration at the vinyl-bearing stereogenic center.

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页码：573 / 576

页数：4

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