Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

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Title: Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones
Authors: Lahosa, Alejandro | Yus, Miguel | Foubelo, Francisco
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Chiral sulfinyl imines | β-amino ketones | Diastereoselective Mannich reactions | Enantioselective synthesis | Piperidine alkaloids
Knowledge Area: Química Orgánica
Issue Date: 7-May-2019
Publisher: American Chemical Society
Citation: The Journal of Organic Chemistry. 2019, 84(11): 7331-7341. doi:10.1021/acs.joc.9b01008
Abstract: Enantiopure β-amino ketone derivatives were synthesized by decarboxylative Mannich reaction of chiral N-tert-butanesulfinyl imines with β-keto acids and were subsequently transformed into cis-2,6-disubstituted piperidin-4-ones through an organocatalyzed condensation with aldehydes. Both enantiomers were accessible from the same precursors by inverting the order in the reaction sequence of the aldehydes involved in the imine formation and the intramolecular Mannich condensation. The synthesis of the piperidine alkaloids (+)-241D, (−)-epimyrtine, and (−)-lasubine II demonstrated the utility of this methodology.
Sponsor: We acknowledge the continued financial support from the Spanish Ministerio de Economía y Competitividad (MINECO; projects CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante.
URI: http://hdl.handle.net/10045/92755
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/acs.joc.9b01008
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 American Chemical Society
Peer Review: si
Publisher version: https://doi.org/10.1021/acs.joc.9b01008
Appears in Collections:INV - SINTAS - Artículos de Revistas

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