Journal
ORGANIC LETTERS
Volume 10, Issue 21, Pages 4839-4842Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8019204
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Funding
- National Cancer Institute [CA-081635]
- Schering-Plough Research Institute
- Royal Thai Government
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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. Rheniurn(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.
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