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


Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Lanier, ML; Kasper, AC; Kim, H; Hong, J

Published Date

  • May 2014

Published In

Volume / Issue

  • 16 / 9

Start / End Page

  • 2406 - 2409

PubMed ID

  • 24724535

Pubmed Central ID

  • 24724535

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol500773w


  • eng