Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis
2008
Radical Cascades in Organic Chemistry
publication
Evidence: moderate
Author Information
Author(s): Hodgson David M, Winning Leonard H
Primary Institution: University of Oxford
Hypothesis
Can radical cascades using enantioenriched 7-azabenzonorbornenes be effectively applied in synthesis?
Conclusion
The study demonstrates a new route to substituted 2-aza-5,6-benzonorbornenes, which can lead to important pharmaceutical compounds.
Supporting Evidence
- The study provides examples of radical rearrangements leading to new chemical structures.
- Electrophile trapping was shown to be effective in synthesizing complex molecules.
- High enantiomeric ratios were achieved in the asymmetric hydroboration process.
Takeaway
This research shows how certain chemical reactions can create complex molecules that might be useful in medicine.
Methodology
The study involved tandem deoxygenation, rearrangement, and electrophile trapping using xanthates from 7-azabenzonorbornadienes.
Limitations
The yields of some reactions were modest and the product profiles were inconsistent.
Digital Object Identifier (DOI)
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