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

Sweeney, Joseph Bernard and Adams, Kirsty and Doulcet, Julien and Thapa, Bimod and Tran, Fanny and Crook, Robert (2018) Optimizing the Mizoroki–Heck reaction of cyclic allyl amines:Gram-scale synthesis of preclamol without protecting groups. Journal of Catalysis, 360. pp. 97-101. ISSN 0021-9517

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Abstract

Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligating heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underexplored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of our study designed to deliver an optimized, scalable MH procedure for N-alkyltetrahydropyridines and its exemplification in a gram-scale synthesis of the drug substance preclamol.

Item Type:
Journal Article
Journal or Publication Title:
Journal of Catalysis
Additional Information:
This is the author’s version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, 360, 2018 DOI: 10.1016/j.jcat.2018.01.007
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
ID Code:
123666
Deposited By:
Deposited On:
23 Feb 2018 09:56
Refereed?:
Yes
Published?:
Published
Last Modified:
01 Oct 2020 02:25