Synfacts 2009(6): 0678-0678  
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

Contributor(s): Benjamin List, Frank Lay
Y.-G. Wang, T. Kumano, T. Kano, K. Maruoka*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
25 May 2009 (online)


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.