Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters To Prepare Acetoxy 4-Alkylidenecyclopent-3-en-2-ones

被引：22

作者：

Brummond, Kay M. ^{[1
]}

Davis, Matthew M. ^{[1
]}

Huang, Chaofeng ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

基金：

美国国家卫生研究院;

关键词：

PAUSON-KHAND REACTION; ASYMMETRIC-SYNTHESIS; TANDEM; CYCLOISOMERIZATION; REARRANGEMENTS; ALCOHOLS; ACETATES; ACCESS; ETHERS; ROUTE;

D O I：

10.1021/jo901459t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(I)-catalyzed cyclocarbonylation reaction of allenol esters has been examined and its synthetic viability established for the conversion of trisubstituted allenes to bicyclo[4.3.0] and -[5.3.0] skeletons possessing an alpha-acetoxy cyclopentadienone. Tetrasubstituted allenol acetates gave elimination products, providing examples of a cyclocarbonylation reaction between an alkyne and it latent cumulene or cumulene equivalent. Cleavage of the acetate affords a free hydroxyl group illustrating the utility of this method for accessing alpha-hydroxy carbonyls from allenol esters.

引用

页码：8314 / 8320

页数：7

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