Oxidative cyclization of diols derived from 1,5-dienes: formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; formal synthesis of (+)-cis-solamin.

Journal article

(Chemical Equation Presented) High yields and high levels of stereocontrol are observed in the oxidative cyclization of vicinal diols using catalytic amounts of a transition metal (see scheme; TFA = trifluoroacetic acid). The product stereochemistry is controlled completely by the starting material, and, importantly, single enantiomers can be accessed readily. The reaction sequence is demonstrated in a very short formal synthesis of the natural product (+)-cis-solamin. © 2005 Wiley-VCH Verlag GmbH and Co. KGaA.

Authors: Donohoe, T; Butterworth, S

• Journal: Angewandte Chemie (International ed. in English)
• Volume: 44
• Issue: 30
• Pages: 4766-4768
• Publication date: 2005-07-01
• DOI: 10.1002/anie.200500513
• EISSN: 1521-3773
• ISSN: 1433-7851
• Language: English
• Keywords: Molecular Conformation; Stereoisomerism; Oxidation-Reduction; Benzethonium; Cyclization; Alkenes; Furans; Osmium Tetroxide; Catalysis