Improved Protocol for Asymmetric, Intramolecular Heteroatom Michael Addition Using Organocatalysis: Enantioselective Syntheses of Homoproline, Pelletierine, and Homopipecolic Acid

An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been acco...

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Veröffentlicht in:	Journal of organic chemistry 2008-07, Vol.73 (13), p.5155-5158
Hauptverfasser:	Carlson, Erik C, Rathbone, Lauren K, Yang, Hua, Collett, Nathan D, Carter, Rich G
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Molecular Structure Organic chemistry Pipecolic Acids - chemical synthesis Piperidines - chemical synthesis Preparations and properties Proline - analogs & derivatives Proline - chemical synthesis
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Zusammenfassung:	An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo800749t