Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.
A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.
Turunen
Brandon J
BJ
Department of Medicinal Chemistry and Center for Methodology and Library Development, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Georg
Gunda I
GI
D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D006573:Heterocyclic Compounds, 1-Ring; D006574:Heterocyclic Compounds, 2-Ring