Intramolecular azide trapping of the nazarov intermediate: Formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation

被引：52

作者：

Rostami, Ali ^{[1
]}

Wang, Yong ^{[1
]}

Arif, Atta M. ^{[1
]}

McDonald, Robert ^{[1
]}

West, F. G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 04期

关键词：

D O I：

10.1021/ol070053m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cross-conjugated dienones with pendent azide side chains undergo interrupted Nazarov trapping, leading to peroxy-bridged indolizidinones in good yields. This process is proposed to involve skeletal rearrangement of the initial trapping product, with loss of dinitrogen, to give an intermediate 1,4-betaine, which then undergoes reaction with atmospheric oxygen. The endoperoxide products can be reduced under catalytic hydrogenation conditions to furnish alpha-hydroxylactams.

引用

页码：703 / 706

页数：4