Abstract
An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 2196-2201 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 2017 Jan 1 |
Keywords
- Lewis acids
- amides
- amines
- cyclization
- diastereoselectivity
- halogenation
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Cite this
Yeh, M-C. P., Chang, Y. M., & Lin, H. H. (2017). Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides. Advanced Synthesis and Catalysis, 359(13), 2196-2201. https://doi.org/10.1002/adsc.201700271