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Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

ABSTRACT: Cyclic enaminones were synthesized in high yields from amino acids in two steps via Wolff rearrangement. The cyclization represents a rare 6-exo-dig cyclization involving a ketene as an electrophile. No racemization was observed during this reaction.

SUBMITTER: Seki H 

PROVIDER: S-EPMC2974010 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

Seki Hajime H   Georg Gunda I GI  

Journal of the American Chemical Society 20101101 44

Cyclic enaminones were synthesized in high yields from amino acids in two steps via Wolff rearrangement. The cyclization represents a rare 6-exo-dig cyclization involving a ketene as an electrophile. No racemization was observed during this reaction. ...[more]

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