Stereoselective Epoxidation of Cyclic Dienes and Trienes by Dioxiranes |
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Authors: | Lucia D'Accolti Cosimo Annese Antonella Aresta Caterina Fusco |
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Institution: | 1. Dipartimento di Chimica, Università di Bari “A. Moro”, Bari, Italy;2. CNR‐ICCOM, Dipartimento di Chimica, Università di Bari, Bari, Italy |
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Abstract: | 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. |
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