DIASTEREOFACIAL SELECTIVITY IN UNCATALYZED DIELS-ALDER CYCLOADDITIONS INVOLVING ALPHA, BETA-UNSATURATED ESTERS AND LACTONES WITH STEREOGENIC CENTERS CONTAINING OXYGEN FUNCTIONALITIES

被引：51

作者：

CASAS, R

PARELLA, T

BRANCHADELL, V

OLIVA, A

ORTUNO, RM

GUINGANT, A

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN

[2] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,UNITE CHIM ORGAN ASSOCIEE 476,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON | 1992年 / 48卷 / 13期

关键词：

D O I：

10.1016/S0040-4020(01)88527-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both experimental and theoretical studies on the Diels-Alder cycloadditions of dienophiles 1, 2 and 3 to different dienes show that the observed diastereofacial selectivity results from a combination of electronic and steric interactions. The traditional Felkin-Anh model is not appropriate for these cases. Several new chiral synthetic building blocks have been prepared.

引用

页码：2659 / 2680

页数：22

共 41 条

[1]

ANH NT, 1977, NOUV J CHIM, V1, P61

[2] DIELS-ALDER CYCLO-ADDITIONS OF CHIRAL BUTENOLIDES WITH CYCLOPENTADIENE - ENDO EXO SELECTIVITY [J].