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- W4254328642 abstract "A new method for the asymmetric synthesis of 1-substituted tetrahydroisoquinolines is presented. It is based on stereoselective addition reactions of organometallic compounds to the intermediate N-acyliminium ion 6, which is provided with an N-acyl group as a chiral auxiliary. In addition reactions with organomagnesium and organozinc reagents diastereoselectivities from 70:30 to 95:5 (for 7/8) were observed with the zinc reagents in general leading to markedly improved stereoselectivities. By catalytic hydrogenation of 7 and 8 and after removal of the chiral auxiliary the target compounds 11 and 12 were obtained. The enantiomerically pure 11c–g and 12c–g (ee > 99 %), 1-aryl-tetrahydroisoquinolines, were evaluated for their affinity to the PCP [1-(1-phenylcyclohexyl)piperidine] binding site of the NMDA (N-methyl D-aspartate) receptor. In each case the enantiomers 11 exhibited a higher affinity than those of 12, with the potencies of the enantiomers differing by a factor of 4 (11/12g) to 27 (11/12c). The absolute configuration of the more potent enantiomers 11 is in accordance with the stereochemical requirement found for FR115427 (3) which is a close analogue." @default.
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- W4254328642 date "1998-09-01" @default.
- W4254328642 modified "2023-09-26" @default.
- W4254328642 title "Asymmetric Synthesis and Enantioselectivity of Binding of 1-Aryl-1,2,3,4-tetrahydroisoquinolines at the PCP Site of the NMDA Receptor Complex" @default.
- W4254328642 doi "https://doi.org/10.1002/(sici)1099-0690(199809)1998:9<2019::aid-ejoc2019>3.3.co;2-k" @default.
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