Every once in a while, our work with synthetic methodology leads us into uncharted territory that is filled with surprises. Since we love mechanism problems as much as anybody, we thought it would be fun to present you with a few of these interesting reactions to play with. The "answers" can be found in the references noted.
References
1. Syntheses and Rearrangements of Spirocyclic Oxaziridines Derived from Unsymmetrical Ketones. Aubé, J.; Hammond, M.; Gherardini, E.; Takusagawa, F. J. Org. Chem. 1991, 56, 499-508. Correction: Idem., Ibid., J. Org. Chem. 1991, 56, 4086.
2. New Copper(I)-Catalyzed Reactions of Oxaziridines: Stereochemical Control of Product Distribution. Aubé, J.; Peng, X.; Wang, Y.; Takusagawa, F. J. Am. Chem. Soc. 1992, 114, 5466-5467.
3. Conformational Analysis and Structural Elucidation of Spirocyclic Oxaziridines Using NMR, Crystallography, and Molecular Modeling. Usuki, Y.; Wang, Y.; Aubé, J. J. Org. Chem. 1995, 60, 8028-8035.
4. Synthesis of a-Amino-a'-diazomethyl Ketones Via Ring Opening of Substituted Cyclopropanones with Alkyl Azides. A Facile Route to N-Substituted 3-Azetidinones. Desai, P.; Aubé, J. Org. Lett. 2000, 2, 1657-1659.
5. Intramolecular Reactions of Benzylic Azides with Ketones: Competition between Schmidt and Mannich Pathways. Wrobleski, A.; Aubé, J. J. Org. Chem. 2001, 66, 886-889.
For More Information Contact:
Department of Medicinal Chemistry
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Tel: 785-864-4495
FAX: 785-864-5326
Internet: jaube@ku.edu
