- Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.
Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.
Journal of the American Chemical Society (2015-03-15)
Travis C McMahon, Jose M Medina, Yun-Fang Yang, Bryan J Simmons, K N Houk, Neil K Garg
PMID25768436
ABSTRACT
We report the generation of the first 3,4-piperidyne and its use as a building block for the synthesis of annulated piperidines. Experimental and computational studies of this intermediate are disclosed, along with comparisons to the well-known 3,4-pyridyne. The distortion/interaction model is used to explain the observed regioselectivities.
MATERIALS
Product Number
Brand
Product Description
Sigma-Aldrich
Benzyl 4-(trifluoromethylsulfonyloxy)-3-(trimethylsilyl)-5,6-dihydropyridine-1(2H)-carboxylate