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Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization

Abstract : A novel aza-Prins cyclization promoted by a synergistic combination between a Lewis acid and a Brønsted acid to efficiently afford piperidines is described. Contrary to what has been previously reported in the literature, the generality of the reaction employing N-alkyl, N-aryl, and nonprotected homoallylamines has been demonstrated. The reaction is highly diastereoselective depending on the homoallylic amine used, N-PMP homoallyl amine leading preferentially to the trans diastereomer, and free homoallylamine affording the deprotected piperidine as single cis diastereomer
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01256843
Contributor : Laurent Jonchère <>
Submitted on : Friday, January 15, 2016 - 1:50:11 PM
Last modification on : Thursday, March 5, 2020 - 2:07:13 PM

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Vianney Durel, Claudia Lalli, Thierry Roisnel, Pierre van de Weghe. Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization. Journal of Organic Chemistry, American Chemical Society, 2016, 81 (3), pp.849-859. ⟨10.1021/acs.joc.5b02342⟩. ⟨hal-01256843⟩

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