STEREOSELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO 1-SUBSTITUTED 3,3-METHYLENE-5,5-DIMETHYL-2-PYRROLIDINONES

被引：11

作者：

JAROSKOVA, L

FISERA, L

MATEJKOVA, I

ERTL, P

PRONAYOVA, N

机构：

[1] SLOVAK UNIV TECHNOL BRATISLAVA, DEPT ORGAN CHEM, BRATISLAVA 81237, SLOVAKIA

[2] COMENIUS UNIV BRATISLAVA, INST CHEM, BRATISLAVA 84215, SLOVAKIA

[3] SLOVAK UNIV TECHNOL BRATISLAVA, CHEM TECH CENT LAB, BRATISLAVA 81237, SLOVAKIA

来源：

MONATSHEFTE FUR CHEMIE | 1994年 / 125卷 / 12期

关键词：

1,3-DIPOLAR CYCLOADDITION OF NITRONES; REGIO- AND STEREOSELECTIVITY OF 1,3-DIPOLAR CYCLOADDITION; AM1; CALCULATIONS;

D O I：

10.1007/BF00811091

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselectivity of the nitrone cycloaddition with 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones 1 is discussed. C,N-Diarylnitrones give mixtures of diastereomeric spirocycloadducts 3 and 4, in which 3 always dominates. In contrast, N-methylnitrones react under the formation of 4 as major products. Cycloaddition of C-benzoyl nitrones 7 with 1 affords exclusively single isoxazolidines 8. Semi-empirical quantum mechanical methods (AM1) were used to rationalize the regio- and stereoselectivity of the reactions.

引用

页码：1413 / 1425

页数：13

共 13 条

[1] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].