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16 The major diastereomeric product in each case results via more stable chair TS in which Me and O − at the two stereocentres of the substrate occupy less-hindered equatorial positions. The stereochemistry of anionic oxy-Cope rearrangement is illustrated with two diastereomeric substrates and having E,E and E,Z stereochemistry of double bonds, respectively (Fig. Science / Chemistry / Physical & Theoretical,Įrnest L.