Stereoselective Epoxidation of Cyclic Dienes and Trienes by Dioxiranes

被引：3

作者：

D'Accolti, Lucia ^{[1
]}

Annese, Cosimo ^{[1
]}

Aresta, Antonella ^{[1
]}

Fusco, Caterina ^{[2
]}

机构：

[1] Univ Bari A Moro, Dipartimento Chim, I-70126 Bari, Italy

[2] Univ Bari, Dipartimento Chim, CNR ICCOM, I-70126 Bari, Italy

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2014年 / 51卷 / 05期

关键词：

DIMETHYLDIOXIRANE; REACTIVITY; OXIDATIONS; CONVERSION; ALCOHOLS;

D O I：

10.1002/jhet.1839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxides are essential building blocks in organic chemistry. The epoxidation of unsubstituted cyclic dienes 2, 3, 4 and triene 5 using dimethyldioxirane (1a) and its trifluoro analog 1b methyl(trifluoromethyl)dioxirane has been investigated. The excellent yields obtained (90-98%) are accompanied by outstandingly high diastereoselectivities (90-98%). Interpretation of results based upon the early idea that polar groups can direct the dioxirane attack by dipole-dipole interaction provides a likely rationale, along with a more generalized mechanistic view.

引用

收藏

页码：1482 / 1486

页数：5

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