Journal article
Temperature Effects on Stereocontrol in the Horner−Wadsworth−Emmons Condensation of α-Phosphono Lactones
Journal of organic chemistry, Vol.72(16), pp.6263-6265
08/03/2007
DOI: 10.1021/jo070722+
PMID: 17629340
Abstract
The Horner−Wadsworth−Emmons condensation of some α-phosphono lactones has been examined for conditions that impact product stereochemistry. The temperature employed to quench the reaction was found to be a major factor. For example, after the diethyl phosphonate derivative of γ-butyrolactone was treated with potassium hexamethyldisilazane, 18-crown-6, and propionaldehyde at −78 °C in THF, an aliquot transferred to a flask at ∼30 °C gave almost exclusively the Z-olefin product, while one allowed to warm to room temperature over several hours greatly favored the E-olefin.
Details
- Title: Subtitle
- Temperature Effects on Stereocontrol in the Horner−Wadsworth−Emmons Condensation of α-Phosphono Lactones
- Creators
- Jose S YuDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.72(16), pp.6263-6265
- DOI
- 10.1021/jo070722+
- PMID
- 17629340
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Language
- English
- Date published
- 08/03/2007
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985883802771
Metrics
12 Record Views