FLUORINATED ALCOHOLS AS SOLVENTS FOR DIELS-ALDER REACTIONS OF CHIRAL ACRYLATES

被引：23

作者：

CATIVIELA, C ^{[1
]}

GARCIA, JI ^{[1
]}

MAYORAL, JA ^{[1
]}

ROYO, AJ ^{[1
]}

SALVATELLA, L ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)80368-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Fluorinated alcohols increase the rates and endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (-)-menthyl and (-)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (-)-menthyl acrylate, but decreases it when the dienophile is (-)-8-phenylmethyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.

引用

页码：1613 / 1618

页数：6

共 20 条

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