Synfacts 2007(9): 0912-0912  
DOI: 10.1055/s-2007-968914
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Reduction of Pyridines via Brønsted Acid Catalysis

Contributor(s): Victor Snieckus, Yigang Zhao
M. Rueping*, A. P. Antonchick
Johann Wolfgang Goethe-Universität Frankfurt, Germany
Further Information

Publication History

Publication Date:
23 August 2007 (online)


An organocatalytic enantioselective reduction of 2-substituted simple and fused pyridines is reported. The reaction is designed to undergo catalytic protonation by Brønsted acid 1, followed by reduction by hydride transfer from the Hantzsch dihydropyridine 2. The hexahydroquinolinone and tetrahydropyridine products are formed in moderate to good yields with good enantioselectivities. The scope of the reaction was modestly investigated.