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

Conor S Barry; Nick Bushby; John R Harding; Rachael A Hughes; Gregory D Parker; Richard Roe; Christine L Willis

doi:10.1039/b504562b

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

Chem Commun (Camb). 2005 Aug 7:(29):3727-9. doi: 10.1039/b504562b. Epub 2005 Jun 16.

Authors

Conor S Barry¹, Nick Bushby, John R Harding, Rachael A Hughes, Gregory D Parker, Richard Roe, Christine L Willis

Affiliation

¹ School of Chemistry, University of Bristol, Cantock's Close, Bristol, UKBS8 1TS. chris.willis@bristol.ac.uk.

PMID: 16027925
DOI: 10.1039/b504562b

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry
Alcohols / chemistry
Catechols / chemistry
Cyanides / chemistry
Cyclization
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Hydrogen / chemistry*
Hydroxylation
Molecular Structure

Substances

Acetals
Alcohols
Catechols
Cyanides
Heterocyclic Compounds
Hydrogen