Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

被引：13

作者：

Cimarelli, C ^{[1
]}

Palmieri, G ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 5-6期

关键词：

D O I：

10.1016/S0040-4020(97)10333-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：915 / 926

页数：12

共 24 条

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