A Highly Divergent Synthesis of 3-Aminotetrahydropyridines
- 19 June 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (12), 8245-8252
- https://doi.org/10.1021/acs.joc.0c00853
Abstract
Dihapto-coordinate 1,2-dihydropyridine complexes of the metal fragment {WTp(NO)(PMe3)} (Tp = tris(pyrazolyl)borate), derived from pyridine, are demonstrated to undergo protonation at C6 followed by regioselective amination at C5 with a variety of primary and secondary amines. The addition takes place stereoselectively anti to the metal center, producing exclusively cis-disubstituted products. The resulting 1,2,5,6-tetrahydropyridines can be successfully liberated by oxidation, providing a route to novel molecules of potential medicinal interest.Funding Information
- National Institutes of Health (1R01GM132205)
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