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AMINOCYCLANOLS .2. STEREOCHEMICAL STUDIES ON A NEW CIRAMADOL ANALOG BY NMR-SPECTROSCOPY

1994-12-01
BURGEMEISTER, T
OZARSLAN, O
ERTAN, M
AKGUN, H
WIEGREBE, W
The absol. configuration of a Ciramadol analogue obtained from (-)-menthone is established by H-1-NMR-, simulated NMR-, COSY-90-, and NOE-measurements. The final compound 2-(alpha-1-pyrrolidino)benzyl-4-isopropyl-1-methyl-cyclohexan-3-one (4b), e.g., has 1R,2S,4S,11S-configuration due to stereoselective Michael-type addition of pyrrolidine to the pertinent benzylidene intermediate 3.