Journal of Organic Chemistry p. 849 - 859 (2016)
Update date:2022-08-11
Topics:
Durel, Vianney
Lalli, Claudia
Roisnel, Thierry
Weghe, Pierre Van De
A novel aza-Prins cyclization promoted by a synergistic combination between a Lewis acid and a Br?nsted 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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