Isoquinoline homogeneous catalysis

Hydrogenation with homogeneous catalysis has received increasing attention over the last few decades. Hexarhodium hexadecacarbonyl (181 Scheme 35) under water gas shift conditions forms 1,2,3,4-tetrahydroquinoline (128) or N-formyl-1,2,3,4-tetrahydroisoquinoline (182) with the parent hete-roaromatic. When hydrogen is substituted for carbon monoxide, 4-methylquinoline is reduced to 4-methyl-5,6,7,8-tetrahydroquinoline (183) exclusively.Isoquinoline behaves similarly generating A/-formyl-l,2,3,4-tetrahydroisoquinoline (184). Similar reductions under water gas shift or synthesis gas conditions using transition metal carbonyls derived from Mn, Co and Fe, have been recorded.Promotion by phase transfer agents is observed in some cases. 

Noyori R, Ohta M, Hsiao Y, Kitamura M, Ohta T, Takaya H (1986) Asymmetric synthesis of isoquinoline alkaloids by homogeneous catalysis. I Am Chem Soc 108 7117-7119... 

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