Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates

Masahiro Yoshida; Kouki Kinoshita; Kosuke Namba

doi:10.1039/C3OB42510J

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Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates†

Masahiro Yoshida,*^a Kouki Kinoshita^a and Kosuke Namba^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan
E-mail: yoshi@tokushima-u.ac.jp

Abstract

A palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates is described. 2-Vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines were produced from the reaction of β-enaminocarbonyl compounds with 1,4-diacetoxy-2-butene and 2-methylene-1,3-propanediol diacetate, respectively.

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DOI: https://doi.org/10.1039/C3OB42510J
Article type: Paper
Submitted: 16 Dec 2013
Accepted: 11 Feb 2014
First published: 12 Feb 2014

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Org. Biomol. Chem., 2014,12, 2394-2403

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Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates

M. Yoshida, K. Kinoshita and K. Namba, Org. Biomol. Chem., 2014, 12, 2394 DOI: 10.1039/C3OB42510J

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Organic & Biomolecular Chemistry

Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates†

Abstract

Supplementary files

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Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates

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