Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.
Publication
, Journal Article
Lanier, ML; Kasper, AC; Kim, H; Hong, J
Published in: Organic Letters
May 2014
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.
Duke Scholars
Published In
Organic Letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
May 2014
Volume
16
Issue
9
Start / End Page
2406 / 2409
Related Subject Headings
- Oxidation-Reduction
- Oxepins
- Organic Chemistry
- Molecular Structure
- Catalysis
- Biological Products
- 03 Chemical Sciences
Citation
APA
Chicago
ICMJE
MLA
NLM
Lanier, M. L., Kasper, A. C., Kim, H., & Hong, J. (2014). Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction. Organic Letters, 16(9), 2406–2409. https://doi.org/10.1021/ol500773w
Lanier, Megan L., Amanda C. Kasper, Hyoungsu Kim, and Jiyong Hong. “Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.” Organic Letters 16, no. 9 (May 2014): 2406–9. https://doi.org/10.1021/ol500773w.
Lanier ML, Kasper AC, Kim H, Hong J. Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction. Organic Letters. 2014 May;16(9):2406–9.
Lanier, Megan L., et al. “Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.” Organic Letters, vol. 16, no. 9, May 2014, pp. 2406–09. Epmc, doi:10.1021/ol500773w.
Lanier ML, Kasper AC, Kim H, Hong J. Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction. Organic Letters. 2014 May;16(9):2406–2409.
Published In
Organic Letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
May 2014
Volume
16
Issue
9
Start / End Page
2406 / 2409
Related Subject Headings
- Oxidation-Reduction
- Oxepins
- Organic Chemistry
- Molecular Structure
- Catalysis
- Biological Products
- 03 Chemical Sciences