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Angew Chem Int Ed Engl. 2009;48(12):2196-200. doi: 10.1002/anie.200804576.

Intermolecular double Prins-type cyclization: a facile and efficient synthesis of 1,6-dioxecanes.

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1
Center for Chemoinformatics Research, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, South Korea.

Abstract

Double or nothing: The title reaction converts a range of aromatic aldehydes and allenylmethyl/allyl silanes into 1,6-dioxecane derivatives in good to excellent yields (see scheme; Ar = aryl, Tf = triflate, THF = tetrahydrofuran, TMS = trimethylsilyl). In addition, the bisdiene product has been transformed into the corresponding tricyclic compound through a Diels-Alder reaction.

PMID:
19204968
DOI:
10.1002/anie.200804576
[Indexed for MEDLINE]
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