A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Karanfil A.Balta B.Eskici M.2024-07-222024-07-22201214645416http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/17507Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline. © 2012 Elsevier Ltd. All rights reserved.English1,2 cyclic sulfamidate derivativealkyl groupamideamino acidconiineesterlithium derivativenorvalinepiperidone derivativeunclassified drugalkylationannulation reactionarticleasymmetric synthesiscyclizationhydrogenationhydrolysisnuclear Overhauser effectpriority journalproton nuclear magnetic resonancering openingstereochemistrysubstitution reactionA [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvalineArticle10.1016/j.tet.2012.09.081