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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.

SUBMITTER: Tadpetch K

PROVIDER: S-EPMC2665917 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Rhenium(VII) catalysis of Prins cyclization reactions.

Tadpetch Kwanruthai K Rychnovsky Scott D SD

Organic letters 20080925 21

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. ...[more]

PMID: 18816133

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