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, Gteborg University, SE-412 96 Gteborg, Sweden, and Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden
Org. Lett., 2003, 5 (22), pp 4085–4088
DOI: 10.1021/ol0354831
Publication Date (Web): October 1, 2003
Copyright © 2003 American Chemical Society
†

 Göteborg University.

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‡

 Stockholm University.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, hilmers@organic.gu.se

Abstract

Abstract Image

SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.

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History

  • Published In Issue October 30, 2003
  • Received August 6, 2003

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