Achmatowicz Reaction

Achmatowicz Reaction

22 March, 2015 / by / in Reactions
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  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • Criteria #4
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  • General Characteristics

Under oxidative conditions, furfuryl alcohol can be converted into dihydropyran. Reagents such as bromine, NBS, and mCPBA are used commonly to effect this type of transformation. In a sense, the furan ring can be viewed as a precursor of 1,4-dicarbonyl compounds.

  • General References

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  • Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105. DOI: 10.1055/s-1998-1584
  • Harris, J. M.;  Li, M.;  Scott, J. G.; O’Doherty, G. A. in Strategy and Tactics in Natural Product Synthesis, ed. M. Harmata, Elsevier, London, 2004, 5, 221–253.
  • Merino, P. Curr. Org. Chem. 2007, 11, 1076.

  • History

In 1971, a Polish chemist Osman Achmatowicz Jr. reported a procedure to synthesize monosaccharides by treating furfuryl alcohol with bromine. This and related reactions are called the Achmatowicz reaction after his name.

Osman Achmatowicz Jr.

  • Reaction Mechanism

Achmatwicz_2.gif

  • Examples

A high yielding example in the synthesis of D-swainsonine.[1]

Achmatwicz_3.gif

  • Experimental Procedure

  • Experimental Tips

  • References

[1] Guo,H.; O’Doherty, G. A. Org. Lett. 2006, 8, 1609. DOI: 10.1021/ol0602811

  • Related Books

[amazonjs asin=”0124171850″ locale=”US” title=”Strategies and Tactics in Organic Synthesis, Volume 10″]

  • External Links

Achmatowicz Reaction (Chemical Christallintiy)

Achmatowicz Reaction – Wikipedia

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