1,3-dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides

被引：20

作者：

Pyne, SG ^{[1
]}

SafaeiG, J ^{[1
]}

Skelton, BW ^{[1
]}

White, AH ^{[1
]}

机构：

[1] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6907,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1995年 / 48卷 / 09期

关键词：

D O I：

10.1071/CH9951511

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered pi-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered pi-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

引用

页码：1511 / 1533

页数：23

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