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Synthesis of ?,?'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.

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 gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided ?,?'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/?-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.

SUBMITTER: Lanier ML

PROVIDER: S-EPMC4018174 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.

Lanier Megan L ML Kasper Amanda C AC Kim Hyoungsu H Hong Jiyong J

Organic letters 20140411 9

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 re ...[more]

PMID: 24724535

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