Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.
Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided α,α'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/α-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.
Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
Megan L
ML
Lanier
Amanda C
AC
Kasper
Hyoungsu
H
Kim
Jiyong
J
Hong
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
D001688:Biological Products; D010082:Oxepins