β-amino acids to piperidinones by petasis methylenation and acid-induced cyclization

被引：18

作者：

Adriaenssens, Louis V. ^{[1
]}

Hartley, Richard C. ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 26期

关键词：

D O I：

10.1021/jo7019948

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Ester-imine derivatives of beta-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Bronsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinones in good yield and diastereoselectivity. The method is analogous to the Petasis-Ferrier rearrangement of 1,3dioxan-4-ones to give tetrahydropyranones.

引用

页码：10287 / 10290

页数：4

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