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Citation: KANG Chuan-Qing, GUO Hai-Quan, QIU Xue-Peng, CHENG Yan-Qin, GAO Lian-Xun. Enantioselective Catalyzed Hydrogenation to Natural Alkaloid Isoanabasine with (S)-BINAP-Rh[J]. Chinese Journal of Applied Chemistry, ;2005, 22(4): 457-459. shu

Enantioselective Catalyzed Hydrogenation to Natural Alkaloid Isoanabasine with (S)-BINAP-Rh

1.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022

Corresponding author: GAO Lian-Xun,
Received Date: 21 October 2004
Available Online: 28 January 2005

The natural alkaloid isoanabasine was prepared by catalytic hydrogenation of tetrahydrobipyridines with (S)-BINAP-Rh complex.The tetrahydrobipyridines bearing bigger N-substituted group displayed high stereoselectivity and low reaction rate.Moreover,the position of the double bond on piperidinene also displayed a great effect on the stereoselectivity that made the ee value of hydrogenation of 1'-benzyl-1',4',5',6'-tetrahydro-2,3'-bipyridine being up to 21.5% but that of 1'-benzyl-1',2',5',6'-tetrahydro-2,3'-bipyridine only being up to 10.0%.
- isoanabasine,
- catalyzed hydrogenation,
- enantioselectivity,
- bipyridine
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