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, ABalta, BEskici, M2024-07-182024-07-180040-4020http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/3645Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding delta-amino-alpha,beta-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. (c) 2012 Elsevier Ltd. All rights reserved.EnglishGLYCOSYL AMINO-ACIDSENANTIOSELECTIVE SYNTHESISSTEREOSELECTIVE-SYNTHESISEFFICIENT SYNTHESISLACTAM PRECURSORSCYCLIC SULFAMATEFACILE ENTRYALPHAREACTIVITYDERIVATIVESA [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-norvalineArticle