Premium
Stereoselective Epoxidation of Cyclic Dienes and Trienes by Dioxiranes
Author(s) -
D'Accolti Lucia,
Annese Cosimo,
Aresta Antonella,
Fusco Caterina
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1839
Subject(s) - dioxirane , dimethyldioxirane , chemistry , stereoselectivity , trifluoromethyl , organic chemistry , polar , dipole , computational chemistry , stereochemistry , medicinal chemistry , catalysis , alkyl , physics , astronomy
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.