Collect. Czech. Chem. Commun. 1991, 56, 954-965

CD of primary amines and 1- or 3-substituted tetrahydroisoquinolines in presence of [Rh2(O2CCH3)4]

Wolfgang Diener, Jadwiga Frelek and Günter Snatzke*

Lehrstuhl für Strukturchemie Ruhr Universität Bochum, Postfach 10 21 48, D 4630 Bochum 1, F.R.G.


The syntheses of (S)-(-)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline (IX) and (S)-(+)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (XVI) [ via (S)-1-benzoyl-N-ethoxycarbonyl ethylamine (XI)] in optically pure form and with known absolute configuration is described. The CD and NMR spectra of these compounds and of most of their intermediates are given, and from these data could be deduced, that the N-methyl groups of the two bases IX and XVI adopt different conformations in solution, but the same (viz. axial) in their complexes with [Rh2(OAc)4].