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Ketyl-allene cyclizations promoted by samarium(II) iodide
Gary A Molander1, Elizabeth Pollina Cormier
1Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
The Journal of Organic Chemistry
|March 25, 2005
Summary
Samarium(II) iodide effectively mediates intramolecular reductive coupling reactions. This study extends this method to cyclizations with allenes, yielding carbocycles and heterocycles.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Samarium(II) iodide is a potent reagent for reductive coupling.
- Previous work demonstrated its efficacy in intramolecular ketyl-olefin cyclizations, forming carbocycles with high yield and diastereoselectivity.
Purpose of the Study:
- To extend the application of samarium(II) iodide-mediated reductive coupling.
- To explore the cyclization of ketyls with allenes for the synthesis of carbocycles and heterocycles.
Main Methods:
- Intramolecular reductive coupling reactions.
- Utilizing samarium(II) iodide as the key reagent.
- Employing allenes as coupling partners in ketyl cyclizations.
Main Results:
- The developed method successfully facilitates ketyl cyclizations with allenes.
- Selective formation of carbocyclic and heterocyclic products was achieved.
- The reaction demonstrates versatility in substrate scope.
Conclusions:
- Samarium(II) iodide is a versatile reagent for synthesizing carbocycles and heterocycles via ketyl-allene cyclizations.
- This methodology offers a selective route to complex cyclic structures.
- The study expands the synthetic utility of samarium(II) iodide in organic synthesis.