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

Vianney Durel | Zendy; Claudia Lalli | Zendy; Thierry Roisnel | Zendy; Pierre van de Weghe | Zendy

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

Author(s) -

Vianney Durel,

Claudia Lalli,

Thierry Roisnel,

Pierre van de Weghe

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b02342

Subject(s) - diastereomer , amine gas treating , chemistry , piperidine , prins reaction , aryl , alkyl , reaction conditions , brønsted–lowry acid–base theory , stereochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis

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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