Stereochemical aspects of novel 5,6-dihydro-4H-1,3-oxazines

被引：13

作者：

Katritzky, AR ^{[1
]}

Ghiviriga, I

Chen, K

Tymoshenko, DO

Abdel-Fattah, AAA

机构：

[1] Univ Florida, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2001年 / 04期

关键词：

D O I：

10.1039/b008196p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel polysubstituted 5,6-dihydro-4H-1,3-oxazines are synthesized by 1,4-cycloaddition of unactivated olefins with N-acyliminiums from benzotriazole precursors. The configuration and conformation of the products are deduced from NMR investigation. The regio- and exo-endo stereochemistry of the cycloaddition are discussed. Conformations of compounds of six types of substitution (6-mono; 6,6-, 5,6- and 4,6-di; 4,6,6- and 4,5,6-tri) are rationalized on the basis of axial-1,3-repulsion and the anomeric effect.

引用

页码：530 / 537

页数：8

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