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Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

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Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland
Laboratoire de Magnétisme Quantique, Ecole Polytechnique Fédérale de Lausanne, BSP 314, Rte de la Sorge, CH-1015 Lausanne, Switzerland
Cite this: J. Org. Chem. 2017, 82, 23, 12318–12327
Publication Date (Web):October 21, 2017
https://doi.org/10.1021/acs.joc.7b02150
Copyright © 2017 American Chemical Society

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    Abstract

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    A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

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    • NMR spectra of all compounds (PDF)

    • X-ray data for 2b·BH3 (CIF)

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    2. Sizhou M. Liu, Dino Wu, Jeffrey W. Bode. One-Step Synthesis of Aliphatic Potassium Acyltrifluoroborates (KATs) from Organocuprates. Organic Letters 2018, 20 (8) , 2378-2381. https://doi.org/10.1021/acs.orglett.8b00720
    3. Bastien Raison, Nicolas Dussart, David Gueyrard. Modified Julia Olefination on Pyrrolidinone: Application to the Total Synthesis of Indolizidine 209D. European Journal of Organic Chemistry 2022, 2022 (27) https://doi.org/10.1002/ejoc.202200334
    4. M. L. Birsa. Carbanions and Electrophilic Aliphatic Substitution. 2020, 343-363. https://doi.org/10.1002/9781119426295.ch8
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