Z-2-PHENYL-4-[(S)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYLEN]-5(4H)-OXAZONE AS THE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS

被引：30

作者：

BUNUEL, E ^{[1
]}

CATIVIELA, C ^{[1
]}

DIAZDEVILLEGAS, MD ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1995年 / 51卷 / 32期

关键词：

D O I：

10.1016/0040-4020(95)00501-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)oxazolone and several cyclic and open chain dienes are studied. Less-reactive dienes required longer reaction times and led to isomerization of the Z-oxazolone and isolation of products derived from the E-isomer; Lewis acid catalysts were used to shorten the reaction times. In all cases high diastereofacial selectivity is observed and Diels-Alder adducts can be obtained in high optical purity. The stereochemistry of adducts has been elucidated by single crystal X-ray structure determinations, H-1-NMR analysis and mechanistic considerations.

引用

页码：8923 / 8934

页数：12

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