AN ENANTIOSELECTIVE SYNTHESIS OF A 6,7-BENZOMORPHAN THROUGH THE CYCLISATION OF THE CHROMIUM TRICARBONYL COMPLEX OF AN 1-(AMINOETHAN-2'-YL)-1,2-DIHYDRONAPHTHALENE

Article abstract of DOI:10.1016/S0040-4039(00)94693-8

(-)-1(S),2(S),4(R),6(R)-1,2,3,4,5,6-Hexahydro-2,6-methano-8-methoxy-1,3,4,6-tetramethyl-3-benzazocine has been synthesised in 86percent enantiomeric excess from the α-(η⁶-chromium tricarbonyl)complex of 1(S),1'(R)-1,2-dihydro-7-methoxy-1,4-dimethyl-1-(N-methyl-N-trifluoroacetamido-1'-methylethan-2'-yl)naphthalene.A precursor of this compound is 2(R),4(S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone which was obtained through an Enders' type C-methylation reaction of 4-(3-methoxyphenyl)-4-methylcyclohexanone using SAMP as the reagent.