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    Rights statement: 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

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

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<mark>Journal publication date</mark>04/2018
<mark>Journal</mark>Journal of Catalysis
Volume360
Number of pages5
Pages (from-to)97-101
Publication StatusPublished
Early online date22/02/18
<mark>Original language</mark>English

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.

Bibliographic note

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