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Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives u...

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Detalles Bibliográficos
Autores principales: Röse, Philipp, Emge, Steffen, Yoshida, Jun-ichi, Hilt, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4361995/
https://www.ncbi.nlm.nih.gov/pubmed/25815067
http://dx.doi.org/10.3762/bjoc.11.18
Descripción
Sumario:The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.