Abstract: Under phase transfer condition enantiomerically pure tetrahydro-β-carboline underwent Aldol condensation and dehydration gave rise to corresponding indoloquinolizine. The Michael addition of indoloquinolizine and methyl malonate showed high stereospecificity which depends on the stereochemistry of the title compounds. In this paper COSY and NOESY of 2D-NMR spectroscopy for 6 indoloquinolizine derivatives were studied. In la and 2a there are NOE relationship between 12b-H and COCH₃ for Ib and 2bhowever there is not any NOE effect at all. In 3a there is NOE relationship between 12b-H and COCH₃; in 3b there is NOE relationship between 6-CO₂CH₃ and COCH₂. Based on these results and Dreiding Stereomodels their configurations, conformations and reactivities of Michael additions with methyl malonate are discussed.

Key words: Indoloquinolizine, 2D-NMR, Stereochemistry