Catalytic, asymmetric, "interrupted" Feist-Bénary reactions.
Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction.
Calter
Michael A
MA
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, USA. mcalter@wesleyan.edu
Phillips
Ryan M
RM
Flaschenriem
Christine
C
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D005663:Furans; D007659:Ketones