Mitsunobu reactions with methanesulfonic acid; the replacement of equatorial hydroxyl groups by azide with net retention of configuration

Davis, A.P.; Dresen, S.; Lawless, L.J.

Mitsunobu reactions with methanesulfonic acid; the replacement of equatorial hydroxyl groups by azide with net retention of configuration

1997

Davis, A.P. | Dresen, S. | Lawless, L.J.

Treatment of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides tn overall yields of 74-87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3 alpha-azidodiol intermediate for steroid-based synthetic receptors.

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