✦ LIBER ✦

Chemo- and diastereoselectivities in the oxidation of cyclopentenols with dimethyldioxirane and methyl(trifluoromethyl)dioxirane

✍ Scribed by Lucia D'Accolti; Michele Fiorentino; Caterina Fusco; Angela M. Rosa; Ruggero Curci

Book ID: 104262385
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 322 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01607-x

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✦ Synopsis

A comparison of the diastereoselectivity and the chemoselectivity (epoxidation versus allylic oxidation) attained in the oxidation of cyclopentenols using dimethyldioxirane and methyl(trifluoromethyl)dioxirane is reported. The results indicate that with both dioxiranes diastereoselective epoxidation of allylic cyclopentenols is accompanied by competitive allylic oxidation to the corresponding enone; for the latter, a likely rationale is proposed.

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