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Synlett 1991; 1991(6): 420-422
DOI: 10.1055/s-1991-20749
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Synthesis of 4,4-Dialkyl-1-iodo-3-buten-2-ones by the Reaction of Tertiary α-Allenic Alcohol Carbamates with N-lodosuccinimide and Aqueous Sodium Bicarbonate

Richard W. Friesen* , Lori G. Phipps
  • *Lash Miller Chemical Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 1A1, Canada
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Publication Date:
07 March 2002 (online)

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Treatment of the carbamate derivatives of tertiary α-allenic alcohols with N-iodosuccinimide in dichloromethane sodium bicarbonate provides (E/Z)-4,4-alkyl-1-iodo-3-buten-2-ones or (E/Z)-4-alkyl-4-aryl-1-iodo-3-buten-2-ones with moderate to excellent stereoselectivity.