Stereoselective radical cascade cyclizations of unsaturated epoxynitriles: Quadruple radical cyclization terminated by a 4-exo process onto nitrile

Radical cascade cyclizations of unsaturated epoxynitriles induced by titanocene chloride proceed in good yields and with excellent diastereoselectivities. From three to seven stereocenters were created by the reaction and a single isomeric product was obtained from most of the substrates examined. T...

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Bibliographic Details
Published inSynlett no. 17; pp. 2718 - 2722
Main Authors Fernandez-Mateos, A., Teijon, P. Herrero, Clemente, R. Rabanedo, Gonzalez, R. Rubio, Gonzalez, F. Sanz
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.10.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cascade reactions
ORGANIC-SYNTHESIS
EPOXIDES
CYCLOBUTANE DERIVATIVES
radical cyclization
titanocene chloride
NATURAL-PRODUCTS
CHEMISTRY
epoxynitriles
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Summary:Radical cascade cyclizations of unsaturated epoxynitriles induced by titanocene chloride proceed in good yields and with excellent diastereoselectivities. From three to seven stereocenters were created by the reaction and a single isomeric product was obtained from most of the substrates examined. The relative configuration of the products is consistent with cyclization occurring via a chair-like transition state. The termination of the radical cascade reaction by 4-exo, 5-exo or 6-exo cyclization onto nitrile is remarkable.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-991057