Literature DB >> 34737462

Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.

Steven Gunawan1, Nathan Bedard1, Christopher Foley1, Christopher Hulme1,2.   

Abstract

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

Entities:  

Keywords:  Bromination; CH-functionalization; Hypervalent iodine; N-Bromosuccinimide; N-acyliminium; Radical

Year:  2021        PMID: 34737462      PMCID: PMC8562708          DOI: 10.1016/j.tetlet.2021.152978

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  11 in total

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Authors:  Peter J. Stang; Viktor V. Zhdankin
Journal:  Chem Rev       Date:  1996-05-09       Impact factor: 60.622

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Authors:  Peter J Stang
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Authors:  Bruce E Maryanoff; Han-Cheng Zhang; Judith H Cohen; Ignatius J Turchi; Cynthia A Maryanoff
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Authors:  Steven Gunawan; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2013-08-14       Impact factor: 2.415

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Authors:  Ronaldo A. Pilli; Dennis Russowsky
Journal:  J Org Chem       Date:  1996-05-03       Impact factor: 4.354

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Authors:  Viktor V Zhdankin; Peter J Stang
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Journal:  Org Lett       Date:  2011-08-31       Impact factor: 6.005

8.  Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis.

Authors:  Raúl E Juárez-Hernández; Scott G Franzblau; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2012-08-16       Impact factor: 3.876

9.  Bioactive conformation of luteinizing hormone-releasing hormone: evidence from a conformationally constrained analog.

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Journal:  Science       Date:  1980-11-07       Impact factor: 47.728

10.  2-Propyl 3,3-dibromo-2-hydroxy-pyrrolidine-1-carboxyl-ate.

Authors:  Gary S Nichol; Steven Gunawan; Zhigang Xu; Justin Dietrich; Christopher Hulme
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-13
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