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Chapters
- 00:04Title
- 00:35Synthesis of (6R)-1-[(R)-1-Phenylethyl)-1-Azoniabicyclo[4.1.0]Heptane Tosylate
- 02:49General Procedure for the Expansion of 1-Azoniabicyclo[4.1.0]Heptane Tosylate
- 03:53Synthesis of (S)-1-[(R)-1-Phenylethyl]azepan-3-ol
- 05:14Synthesis of [(2R,3R,4R)-3,4-Bis(Benzyloxy)-1-(S)-1-Phenylethyl)Piperidin-2-Yl]Methyl Acetate
- 08:03Results: Synthesis and Characterization of Bicyclic Aziridinium Ions and its Ring Expansion to Azaheterocycles
- 09:53Conclusion
Bicyclic aziridinium ions such as 1-azoniabicyclo[4.1.0]heptane tosylate were generated from 2-[4-tolenesulfonyloxybutyl]aziridine, which was utilized for the preparation of substituted piperidines and azepanes via regio- and stereospecific ring-expansion with various nucleophiles. This highly efficient protocol allowed us to prepare diverse azaheterocycles including natural products such as fagomine, febrifugine analogue and balanol.
