Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans

Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

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Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2005-08 (29), p.3727-3729
Hauptverfasser:	Barry, Conor S, Bushby, Nick, Harding, John R, Hughes, Rachael A, Parker, Gregory D, Roe, Richard, Willis, Christine L
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetals - chemistry Alcohols - chemistry Catechols - chemistry Cyanides - chemistry Cyclization Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Hydrogen - chemistry Hydroxylation Molecular Structure
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Beschreibung
Zusammenfassung:	Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/b504562b