Synthesis of α,α′-<i>trans</i>-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
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Abstract
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 <i>gem</i>-disubstituent (Thorpe–Ingold) effect
stereoselectively provided α,α′-<i>trans</i>-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