Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups

Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol... Journal of Catalysis 360 (2018) 97–101 Contents lists available at ScienceDirect Journal of Catalysis journal homepage: www.elsevier.com/locate/jcat Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups a,⇑ b b b Joseph B. Sweeney , Kirsty Adams , Julien Doulcet , Bimod Thapa , c d Fanny Tran , Robert Crook Department of Chemistry, Lancaster University, Lancaster LA1 4YB, UK Department of Chemical Sciences, University of Huddersfield, Huddersfield HD1 3DH, UK Department of Chemistry, University of Reading, Reading RG6 6AP, UK Pfizer Ltd, Ramsgate Road, Sandwich, Kent CT13 9NJ, UK article i nfo abstract Article history: Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a Received 9 November 2017 capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligat- Revised 2 January 2018 ing heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underex- Accepted 9 January 2018 plored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Available online 22 February 2018 Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Catalysis Elsevier

Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier Inc.
ISSN
0021-9517
D.O.I.
10.1016/j.jcat.2018.01.007
Publisher site
See Article on Publisher Site

Abstract

Journal of Catalysis 360 (2018) 97–101 Contents lists available at ScienceDirect Journal of Catalysis journal homepage: www.elsevier.com/locate/jcat Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups a,⇑ b b b Joseph B. Sweeney , Kirsty Adams , Julien Doulcet , Bimod Thapa , c d Fanny Tran , Robert Crook Department of Chemistry, Lancaster University, Lancaster LA1 4YB, UK Department of Chemical Sciences, University of Huddersfield, Huddersfield HD1 3DH, UK Department of Chemistry, University of Reading, Reading RG6 6AP, UK Pfizer Ltd, Ramsgate Road, Sandwich, Kent CT13 9NJ, UK article i nfo abstract Article history: Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a Received 9 November 2017 capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligat- Revised 2 January 2018 ing heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underex- Accepted 9 January 2018 plored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Available online 22 February 2018 Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of

Journal

Journal of CatalysisElsevier

Published: Apr 1, 2018

References

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