Schmidt reaction of (S)-1-(2′, 4′, 6-trimethoxy-4, 6′-dimethylbiphenyl-2-yl)ethanone8 furnished the expected amide9 (43%) accompanied by (S)-2, 7′-dimethoxy-3′, 5′, 6-trimethylspiro[cyclohexa-2, 5-diene-1, 1′-(1H)isoindole]-4-one12 (30%) which on reduction with zinc and acetic acid and subsequent methylation regenerated ketone8.Schmidt rearrangement of the ketone1 provided besides the expected amide2 the dienone3 in which chirality has been transferred from the biphenyl axis to the spiro centre. Reductive cleavage and subsequent methylation of3 regenerated1.