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
| dc.contributor.author | Karanfil, A | |
| dc.contributor.author | Balta, B | |
| dc.contributor.author | Eskici, M | |
| dc.date.accessioned | 2025-04-10T10:28:41Z | |
| dc.date.available | 2025-04-10T10:28:41Z | |
| dc.description.abstract | Regioselective 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. | |
| dc.identifier.issn | 0040-4020 | |
| dc.identifier.uri | http://hdl.handle.net/20.500.14701/35511 | |
| dc.language.iso | English | |
| dc.title | 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 | |
| dc.type | Article |