Green chemistry: solvent- and metal-free Prins cyclization. Application to sequential reactionsElectronic supplementary information (ESI) available: Complete synthetic procedures, characterization data, 1H and 13C NMR spectra of all new compounds. See DOI: 10.1039/c1cc16501a

Prins cyclization between a homoallylic alcohol and an aldehyde, promoted by trimethylsilyl halide, afforded 4-halo-tetrahydropyrans with good to excellent yields. Thanks to the absence of the solvent and metal, the THP thus obtained have been implicated without purification in several other reactio...

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Main Authors: Clarisse, Damien, Pelotier, Béatrice, Piva, Olivier, Fache, Fabienne
Format: Article
Language:English
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Summary:Prins cyclization between a homoallylic alcohol and an aldehyde, promoted by trimethylsilyl halide, afforded 4-halo-tetrahydropyrans with good to excellent yields. Thanks to the absence of the solvent and metal, the THP thus obtained have been implicated without purification in several other reactions, in a sequential way, affording in particular new indole derivatives. A solvent- and metal-free Prins-cyclization reaction was developped to access 4-halo-THP products, which can be sequentially used in several other reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/c1cc16501a