Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.
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.
Department of Chemistry, Institute for Therapeutics Discovery and Development, College of Pharmacy, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, USA.
Hajime
H
Seki
Gunda I
GI
Georg
D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
D000577:Amides; D000596:Amino Acids; D014753:Vinyl Compounds