Concepedia

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

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

Organic Letters · 2014 · 28 citations · 20 references

DOI

Concepts

Abstract

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.

References

20

Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives:  Enantioselective Synthesis of <i>β</i>-Aryl-<i>β</i>-Amino Acids

Anna G. Wenzel, Eric N. Jacobsen · Journal of the American Chemical Society · 2002 · 551 citations

, , +10

Proline‐Catalyzed Mannich Reaction of Aldehydes with <i>N</i>‐Boc‐Imines

Jung Woon Yang, Michael Stadler, Benjamin List · Angewandte Chemie International Edition · 2006 · 191 citations

, , +13

Synthesis of <scp>d</scp>- and <scp>l</scp>-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran

Michael H. Haukaas, George A. O’Doherty · Organic Letters · 2001 · 139 citations

, , +5

Nitrogen Heterocycles From Furans: The Aza-Achmatowicz Reaction

Marco A. Ciufolini, Cynthia Y. W. Hermann, Qing Dong et al. · Synlett · 1998 · 116 citations

, , +17

Lewis Acid-Catalyzed Ring-Opening Reactions of Semicyclic <i>N</i>,<i>O</i>-Acetals Possessing an Exocyclic Nitrogen Atom:  Mechanistic Aspect and Application to Piperidine Alkaloid Synthesis

Masaharu Sugiura, Hiroyuki Hagio, Ryoji Hirabayashi et al. · Journal of the American Chemical Society · 2001 · 99 citations

, , +16