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Synlett 1999; 1999(9): 1399-1400
DOI: 10.1055/s-1999-2866
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A Straightforward Synthesis of α-Furfuryl Amide via Lewis Acid-mediated Allylic Substitution

Xue-Long Sun* , Toshitsugu Kai, Hiroaki Takayanagi, Kimio Furuhata
  • *School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan; Fax + 81-3-34 42-57 07; E-mail: furuhatak@pharm.kitasato-u.ac.jp
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Publication Date:
31 December 1999 (online)

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α-(Methoxycarbonyl)furfuryl amide was prepared by Lewis acid catalyzed allylic substitution reaction of the corresponding α-(methoxycarbonyl)furfuryl carbinol acetate with various nitriles as nucleophiles, and the so-formed amides were subjected to oxidative cleavage of the furan ring to afford N-protected polyhydroxyamino acids.

synthesis - α-furfuryl amide - nitrile - Lewis acid - allylic substitution

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