Rhenium(VII) catalysis of Prins cyclization reactions.
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.
Tadpetch
Kwanruthai
K
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Rychnovsky
Scott D
SD
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D015394:Molecular Structure; D012211:Rhenium / Q000737:chemistry*
D000447:Aldehydes; D012211:Rhenium