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- W2759175631 abstract "Chiral 2-substituted-6-methyl 2,3-dihydropyidinones 9, which can be facilely obtained from an asymmetric vinylogous Mannich reaction (VMR) with 1,3-bis-trimethysily enol ether, were used as versatile intermediates in constructing chiral polyfunctional piperidine-based compounds. The 6-methyl group of such compounds can be conveniently functionalized via alkylation and acylation reactions to provide efficient entries to the synthesis of a variety of chiral multi-substituted piperidine-based compounds. Further elaboration of the corresponding intermediates also provided access to polyfunctional indolizidine-based compounds. These methods were showcased in an asymmetric synthesis of 2,6-di-substituted piperidine compound 13, reported as the key intermediate in the synthesis of (+)-calvine and a natural alkaloid (-)-indolizidine 209D. Furthermore, selective C5 iodination of compound 9 enabled the installation of additional functional groups at this position. Finally, we demonstrated that the oxidative cleavage of 2-substituted-6-methyl-2,3-dihydropyidinones is a practical and efficient method for the enantioselective synthesis of β-amino acids, which can undergo further intra-molecular cyclization to give the corresponding chiral four-membered β-lactam derivatives." @default.
- W2759175631 created "2017-10-06" @default.
- W2759175631 creator A5049692788 @default.
- W2759175631 creator A5087077641 @default.
- W2759175631 date "2017-10-18" @default.
- W2759175631 modified "2023-10-17" @default.
- W2759175631 title "Synthetic versatility of 2-substituted-6-methyl 2,3-dihydropyridinones in the synthesis of polyfunctional piperidine-based compounds and related β amino acid derivatives." @default.
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- W2759175631 doi "https://doi.org/10.1039/c7ob01948c" @default.
- W2759175631 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28975943" @default.
- W2759175631 hasPublicationYear "2017" @default.
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