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 (stereoselectiv...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%.展开更多
文摘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%.
