Palladium-Catalyzed [1,3]-O-to-C Rearrangement of Pyrans toward Functionalized Cyclohexanones

被引：14

作者：

Brioche, Julien C. R. ^{[1
]}

Barker, Thomas A. ^{[1
]}

Whatrup, David J. ^{[2
]}

Barker, Michael D. ^{[3
]}

Harrity, Joseph P. A. ^{[3
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] GlaxoSmithKline Inc, Tonbridge TN11 9AN, Kent, England

[3] GlaxoSmithKline Res & Dev Ltd, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

1,3-OXYGEN-TO-CARBON ALKYL SHIFTS; 2-BENZENESULFONYL CYCLIC ETHERS; MEDIATED REARRANGEMENT; RING-CONTRACTION; STEREOSELECTIVE-SYNTHESIS; ALLYLPALLADIUM COMPLEXES; ALLYLIC ALKYLATION; ACID; ISOMERIZATION; SUBSTITUTION;

D O I：

10.1021/ol102213s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized cyclohexanones are prepared from cyclic enol ethers via a Pd-catalyzed [1,3]-O-to-C rearrangement reaction. alpha-Arylketones are generated with excellent diastereocontrol when basic phosphine ligands are used. In contrast, a Lewis acid is required to promote the rearrangement of the alkyl-substituted enol ether systems.

引用

页码：4832 / 4835

页数：4

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