Journal article
Quinine synthesis studies: a radical-ionic annulation via Mn-mediated addition to chiral N-acylhydrazones
Organic letters, Vol.9(21), pp.4243-4246
10/11/2007
DOI: 10.1021/ol7017938
PMID: 17850094
Abstract
A radical-ionic annulation approach to functionalized perhydroisoquinolines involving Mn-mediated coupling of alkyl iodides and chiral N-acylhydrazones was achieved using only 1.25 equiv of the alkyl iodide. Application of this reaction to alkene-containing substrates en route to quinine offered modest yields, decreasing on scaleup. Control experiments revealed that the alkene interfered with the coupling reaction. A revised approach involving prior oxidation of the alkene offered 93% yield in the Mn-mediated coupling, with the adduct obtained as a single diastereomer.
Details
- Title: Subtitle
- Quinine synthesis studies: a radical-ionic annulation via Mn-mediated addition to chiral N-acylhydrazones
- Creators
- Chandra Sekhar Korapala - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USAJun QinGregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.9(21), pp.4243-4246
- Publisher
- United States
- DOI
- 10.1021/ol7017938
- PMID
- 17850094
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- R01-GM67187 / NIGMS NIH HHS
- Language
- English
- Date published
- 10/11/2007
- Academic Unit
- Chemistry
- Record Identifier
- 9983985845902771
Metrics
19 Record Views