Rhenium(VII) catalysis of Prins cyclization reactions.

Abstract

The rhenium(VII) complex O3ReOSiPh3 is a particularly effective catalyst for Prins cyclizations using aromatic and alpha,beta-unsaturated aldehydes. The reaction conditions are mild, and the highly substituted 4-hydroxytetrahydropyran products are formed stereoselectively. Rhenium(VII) complexes appear to spontaneously form esters with alcohols and to directly activate electron-rich alcohols for solvolysis. Re2O7 and perrhenic acid are equally effective in catalyzing these cyclizations.

DOI: 10.1021/ol8019204

Cite this paper

@article{Tadpetch2008RheniumVIICO, title={Rhenium(VII) catalysis of Prins cyclization reactions.}, author={Kwanruthai Tadpetch and Scott D Rychnovsky}, journal={Organic letters}, year={2008}, volume={10 21}, pages={4839-42} }