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Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

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.

SUBMITTER: McMahon TC

PROVIDER: S-EPMC4502428 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

McMahon Travis C TC Medina Jose M JM Yang Yun-Fang YF Simmons Bryan J BJ Houk K N KN Garg Neil K NK

Journal of the American Chemical Society 20150320 12

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. ...[more]

PMID: 25768436

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