The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp reaction

被引：36

作者：

Clarke, PA ^{[1
]}

Martin, WHC ^{[1
]}

Hargreaves, JM ^{[1
]}

Wilson, C ^{[1
]}

Blake, AJ ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 19期

关键词：

D O I：

10.1039/b508252h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, multi-component reaction for the synthesis of highly substituted tetrahydropyran-4-ones,based on the long forgotten Maitland-Japp reaction has been realised. Two different aldehydes and a derivative of a beta-ketoester can be condensed regioselectively in the presence of a Lewis acid to form tetrahydropyran-4-ones in excellent yields. The diastereoselectively of the reaction was found to be dependant upon the nature of the Lewis acid and the temperature at which the reaction was carried out. This procedure was also extended to the formation of tetrahydropyran-4-ones in greater than 95% enantiomeric excess.

引用

页码：3551 / 3563

页数：13

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