Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2025

Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization

Résumé

A straightforward and highly diastereoselective synthesis of cis-4-hydroxypiperidines is presented. This method allows access to C2 and C4 substituted piperidines, bearing a tetrasubstituted carbon stereocenter at C4. gem-Disubstituted homoallylic amines and ketoaldehydes as carbonyl partners have been rarely used in aza-Prins cyclizations, expanding the scope of this reaction.

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hal-04919312 , version 1 (29-01-2025)

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Myriam Le Roch, Nicolas Gouault, Jacques Renault, Gilles Argouarch, Thierry Roisnel, et al.. Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization. Organic & Biomolecular Chemistry, 2025, 23 (7), pp.1644-1652. ⟨10.1039/d4ob01807a⟩. ⟨hal-04919312⟩
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