Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts

被引：26

作者：

Cativiela, C ^{[1
]}

Fraile, JM ^{[1
]}

Garcia, JI ^{[1
]}

Lopez, MP ^{[1
]}

Mayoral, JA ^{[1
]}

Pires, E ^{[1
]}

机构：

[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 08期

关键词：

D O I：

10.1016/0957-4166(96)00295-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with 2,3-dimethylbutadiene, cyclopentadiene, and 2-methyl-1,3-butadiene (isoprene) are catalysed by silica gel and aluminium, titanium, and zinc catalyst supported on silica gel. Overall conversion and asymmetric induction are obtained with very low percentages of E/Z isomerisation. The best results are obtained with ZnCl2 supported on silica gel, and by carrying out the reaction without a solvent. The stereochemistry of the major cycloadducts has been determined by single crystal X-ray structure determination and AM1 calculations of the corresponding transition structures. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2391 / 2398

页数：8

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