Ti-Mg-Catalyzed Carbozincation of N-Benzyl-N-(but-3-en-1-yl)Hept-2-Yn-1-Amine with Et2Zn

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Abstract

It has been shown for the first time that the Ti-Mg-catalyzed carbozincation reaction of N-benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine with Et2Zn is accompanied by regio- and stereoselective formation of (Z)-1-benzyl-4-methyl-3-pentylidenepiperidine. The effect of the nature of the solvent on the Ti-Mg-catalyzed heterocyclization of N-benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine was studied. A mechanism is proposed for the studied reaction of carbozincation of N-homoallyl-substituted propargylamine with Et2Zn in the presence of catalytic amounts of Ti(O-iPr)4 and EtMgBr.

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About the authors

A. M. Gabdullin

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Email: kadikritan@gmail.com
ORCID iD: 0000-0001-5204-7394
Russian Federation, Ufa

R. N. Kadikova

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Author for correspondence.
Email: kadikritan@gmail.com
ORCID iD: 0000-0002-4636-1739
Russian Federation, Ufa

I. R. Ramazanov

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Email: kadikritan@gmail.com
ORCID iD: 0000-0002-3846-6581
Russian Federation, Ufa

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Supplementary files

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1. JATS XML
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2. Scheme 1. Ti-Mg-Catalysed carbocinylation reaction of N-allyl-substituted 2-alkynylamines

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3. Scheme 2. Ti-Mg-Catalysed carbocinylation reaction of N-benzyl-N-(but-3-en-1-yl)hept-2-in-1-amine

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4. Scheme 3. Putative mechanism of catalytic 2-cincoethylzincination of N-homoallyl-substituted 2-alkynylamines

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5. Scheme 4. Ti-Mg-Catalysed carbocinylation reaction of N-benzyl-N-(but-3-en-1-yl)hept-2-in-1-amine in the medium of different solvents

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6. Scheme 5. Effect of solvent nature on the Ti-Mg-catalysed reaction of N-(but-2-in-1-yl)-N-methylbut-3-en-1-amine with Et2Zn

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7. Scheme 6

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