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Synfacts 2009(6): 0678-0678
DOI: 10.1055/s-0029-1216763
DOI: 10.1055/s-0029-1216763
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Phase-Transfer Catalytic One-Pot Approach to Alkaloid Core Structures
Y.-G. Wang, T. Kumano, T. Kano, K. Maruoka*
Kyoto University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
25. Mai 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200906/lookinside/thumbnails/10.1055-s-0029-1216763-1.jpg)
Significance
The authors present an elegant and highly enantioselective synthesis of pyrrolidine, hexahydropyrrolizine, and octahydroindolizine core structures. Key step is the asymmetric conjugate addition of N-(diphenylmethylene)-glycine ester to α,β-enones catalyzed by chiral phase-transfer catalyst 1. Intramolecular reduc-tive amination and subsequent in situ acetal hydrolysis-reductive amination using Hantzsch ester 2 and trifluoroacetic acid gives access to alkaloid core structures in a simple one-pot procedure.