1 - -1,2,3,4-tetrahydroiso- 1,2,3,4-tetrahydroisoquinoline quinoline

Enantioselective catalytic hydrogenation. The ruthenium(II) complexes of (R)- and (S)-l, bearing a chiral BINAP ligand, catalyze asymmetric hydrogenation of N-acyl-l-alkylidenetetrahydroisoquinolines to give (1R)- or (lS)-tetrahydroiso-quinolines in 95-100% ee.1 Thus the (Z)-enamide (2), prepared by acylation of 3,4-dihydropapaverine, is hydrogenated in the presence of (R)-l to (1R)-tetrahydroisoquinolines (3). The enantiomeric (lS)-3 is obtained on use of (S)-l as catalyst. 

The asymmetric alkynylation of isoquinoline iminium ion was reported in the presence of CuBr/QUINAP system (Scheme 5.7). ° Various alkynyl tetrahydroiso-quinolines were obtained in excellent yields and enantiomeric excesses. A natural product, homolaudanosine, was synthesized by the reduction of the obtained propargyl tetrahydroisoquinoline. 

The reaction of l-phenyl-6,7-diethox -l,2,3,4-tetrahydroiso-quinoline with benzoyl C3 anide in benzene-acetic acid gave rise to 54 which on basic hydrol3 sis yielded l-phenyl-6,7-diethoxy-l,2,3,4-tetrahydroisoquinoline-1 -carboxamide. ... 

The results of a structural investigation of the alkaloid were announced recently (59). The sodium-ammonia reduction of thalmine yielded 1 - (4 - methoxybenzyl) - 2 - methyl - 6 - methoxy -1,2,3,4 - tetrahydroiso -quinoline (XXXIII). ReductivecleavageofO-ethylthalmine(LXXXVII) afforded 1 - (4 -hydroxybenzyl)-2-methyl-6-ethoxy - 7 - methoxy -1,2,3,4-tetrahydroisoquinoline (VIII) and l-(4 -methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-l,2,3,4-tetrahydroisoquinoline (IV). On the basis of these results formula LXXXVI was proposed for the alkaloid. 

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