Synthesis and ring-opening reactions of the diastereoisomeric cis- and trans-epoxides derived from 3-(benzyloxy)cyclopentene and 2-(benzyloxy)-2,5-dihydrofuran

被引：0

作者：

Crotti, P ^{[1
]}

Di Bussolo, V ^{[1
]}

Favero, L ^{[1
]}

Macchia, F ^{[1
]}

Pineschi, M ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan, I-56126 Pisa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 08期

关键词：

epoxides; regioselectivity; nucleophilic additions; synthetic methods;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemical outcome of the ring-opening of epoxides bearing remote polar functionalities has been established in the case of carbocyclic (1 and 2) and the corresponding furanosidic (3 and 4) title epoxides. Under standard conditions, the regioisomeric C-1 products are the sole (from trans epoxides 2 and 4) or predominant (from cis epoxides 1 and 3) ring-opening products. However, under chelating conditions, and only in the case of the cis epoxides 1 and 3, a consistent increase in C-2 selectivity is unexpectedly observed.

引用

页码：1675 / 1686

页数：12

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