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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