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