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

Journal of the American Chemical Society
Travis C McMahonNeil K Garg

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.

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Citations

Feb 9, 2016·Journal of the American Chemical Society·Joyann S BarberNeil K Garg
Mar 19, 2016·Journal of the American Chemical Society·Tejas K ShahNeil K Garg
Aug 4, 2016·Organic Letters·Sung-Eun Suh, David M Chenoweth
Aug 3, 2016·Journal of the American Chemical Society·Noah F Fine NathelNeil K Garg
Jan 15, 2016·Angewandte Chemie·Catherine M HoldenMichael F Greaney
Feb 15, 2017·Chemical Communications : Chem Comm·Yuto HiokiAtsunori Mori
Oct 23, 2015·Chemical Communications : Chem Comm·Amit Kumar Chattopadhyay, Stephen Hanessian
Sep 25, 2017·Organic & Biomolecular Chemistry·Rui FanDasan M Thamattoor
Apr 28, 2017·Angewandte Chemie·F Matthias Bickelhaupt, Kendall N Houk
Jan 26, 2017·Organic & Biomolecular Chemistry·T WezemanS Bräse
Aug 1, 2018·Nature Chemistry·Joyann S BarberNeil K Garg
Sep 30, 2017·Chemical Communications : Chem Comm·Elodie DecuypèreFrédéric Taran
Sep 21, 2017·Angewandte Chemie·Peter D Morse, Timothy F Jamison
Nov 27, 2020·Chemical Communications : Chem Comm·Hinano TakemuraSuguru Yoshida
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Mar 26, 2021·Angewandte Chemie·Guanqun ZhangLaura L Anderson
Apr 15, 2021·Angewandte Chemie·Melissa RamirezKendall N Houk
Aug 3, 2021·JACS Au·Sarah M AnthonyNeil K Garg
Jun 4, 2021·Angewandte Chemie·Melissa RamirezNeil K Garg
Mar 7, 2019·The Journal of Organic Chemistry·Jason V ChariNeil K Garg
May 22, 2020·Organic Letters·Matthew S McVeighNeil K Garg
Jan 11, 2019·Journal of the American Chemical Society·Expédite Yen-PonDavide Audisio
Jul 3, 2020·The Journal of Organic Chemistry·Mitchell E LahmHenry F Schaefer
Oct 5, 2018·Journal of the American Chemical Society·Dachuan QiuYang Li
May 3, 2018·Journal of the American Chemical Society·Elias PicazoNeil K Garg

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