Catalytic, asymmetric, aldol/O-conjugate addition sequence for the construction of highly substituted furanoids.
A new method for the enantioselective synthesis of highly functionalized dihydrofurans has been developed. This process, related to the interrupted Feist-Bénary reaction, involves the reaction of 2-ene 1,4-diketones with dimedone in the presence of bis(cinchona alkaloid)pyrimidine catalysts to afford dihydrofuran products in excellent yields and high diastereo- and enantioselectivities.
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, United States.
Michael A
MA
Calter
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, United States.
Alexander
A
Korotkov
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D002930:Cinchona Alkaloids; D005663:Furans; D007659:Ketones; C116609:3-hydroxybutanal