A renewable tertiary hydroperoxide has been efficiently synthesized in 83% overall yield starting from commercially available (+)-endo-2-norborneol. This oxygen donor, derived from (+)-norcamphor, when employed in Ti(O i-Pr)(4)-catalyzed sulfoxidations, proved to be considerably more reactive when compared to a previously reported camphor-derived hydroperoxide. Reduced steric hindrance of the new oxidant lowered the level of asymmetric induction achieved in the oxidation, but stereo-convergent kinetic resolution has been exploited to improve enantioselectivity. Excellent recovery (95%) of the tertiary alcohol at the end of the sulfoxidation provides a highly advantageous chiral resource saving protocol.

Synyhesis of a renewable hydroperoxide from (+)-norcamphor:implications of steric modification of the bicyclic framework on asymmetric sulfoxidation

LATTANZI, Alessandra;SCETTRI, Arrigo
2004

Abstract

A renewable tertiary hydroperoxide has been efficiently synthesized in 83% overall yield starting from commercially available (+)-endo-2-norborneol. This oxygen donor, derived from (+)-norcamphor, when employed in Ti(O i-Pr)(4)-catalyzed sulfoxidations, proved to be considerably more reactive when compared to a previously reported camphor-derived hydroperoxide. Reduced steric hindrance of the new oxidant lowered the level of asymmetric induction achieved in the oxidation, but stereo-convergent kinetic resolution has been exploited to improve enantioselectivity. Excellent recovery (95%) of the tertiary alcohol at the end of the sulfoxidation provides a highly advantageous chiral resource saving protocol.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/1058689
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