SmI₂/Water/Amine Mediates Cleavage of Allyl Ether Protected Alcohols: Application in Carbohydrate Synthesis and Mechanistic Considerations

Anders Dahlén, Andreas Sundgren, Martina Lahmann, Stefan Oscarson and Göran Hilmersson*

*Department of Chemistry, Göteborg University, SE-412 96 Göteborg, Sweden, Email: hilmersorganic.gu.se

A. Dahlen, A. Sundgren, M. Lahmann, S. Oscarson, G. Hilmersson, Org. Lett., 2003, 5, 4085-4088.

DOI: 10.1021/ol0354831

Abstract

Selective cleavage of unsubstituted allyl ethers is provided by SmI₂/H₂O/i-PrNH₂ in very good yields. This method is useful in the deprotection of alcohols and carbohydrates.

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Key Words

Allyl Ethers, Cleavage, Deprotection, Samarium

ID: J54-Y2003-470

SmI2/Water/Amine Mediates Cleavage of Allyl Ether Protected Alcohols: Application in Carbohydrate Synthesis and Mechanistic Considerations

Anders Dahlén, Andreas Sundgren, Martina Lahmann, Stefan Oscarson and Göran Hilmersson*

SmI₂/Water/Amine Mediates Cleavage of Allyl Ether Protected Alcohols: Application in Carbohydrate Synthesis and Mechanistic Considerations