Radical reactions of epoxy esters induced by titanocene chloride

The reductive radical cyclizations of several epoxy esters have been achieved using titanocene chloride. The tether length from the initial radical to the carbonyl acceptor is the key of the reactions. We obtained products from radical cyclization onto carbonyl formate and products from formate and...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 44; pp. 7755 - 7758
Main Authors Fernández-Mateos, A., Herrero Teijón, P., Rabanedo Clemente, R., Rubio González, R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.10.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXIDES
ALDEHYDE
NATURAL-PRODUCTS
STEREOCHEMISTRY
CHEMISTRY
INTRAMOLECULAR ADDITION
CYCLIZATION
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Summary:The reductive radical cyclizations of several epoxy esters have been achieved using titanocene chloride. The tether length from the initial radical to the carbonyl acceptor is the key of the reactions. We obtained products from radical cyclization onto carbonyl formate and products from formate and hydrogen elimination. The stereochemical outcome of the 5- exo radical cyclization of two diastereomers is reported. A radical cascade cyclization of an unsaturated epoxy formate is also described.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.08.124