Organocatalytic Entry into 2,6-Disubstituted Aza-Achmatowicz
Piperidinones: Application to (−)-Sedacryptine and Its Epimer

van der Pijl, Ferdi; Harmel, Robert
K.; J. J. Richelle, Gaston; Janssen, Peter; L. van Delft, Floris; P. J. T. Rutjes, Floris

doi:10.1021/ol500633u.s001

Organocatalytic Entry into 2,6-Disubstituted Aza-Achmatowicz Piperidinones: Application to (−)-Sedacryptine and Its Epimer

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posted on 2014-04-04, 00:00 authored by Ferdi van der Pijl, Robert K. Harmel, Gaston J. J. Richelle, Peter Janssen, Floris L. van Delft, Floris P. J. T. Rutjes

Enantiomerically pure 2,6-disubstituted piperidinones were synthesized from furfural involving an organocatalyzed Mannich reaction, aza-Achmatowicz reaction, and an N-acyliminium ion-mediated coupling step. This approach was also successfully applied to a total synthesis of (−)-sedacryptine and one of its epimers.

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epimer furfural Application Sedacryptine sedacryptine approach synthesis organocatalyzed Mannich reaction Disubstituted Organocatalytic Entry Piperidinone EpimerEnantiomerically disubstituted piperidinone

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Organocatalytic Entry into 2,6-Disubstituted Aza-Achmatowicz Piperidinones: Application to (−)-Sedacryptine and Its Epimer

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