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

Lattanzi, Alessandra; Iannece, P.; Scettri, Arrigo

doi:10.1016/j.tetasy.2004.04.027

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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.

Titolo:	Synyhesis of a renewable hydroperoxide from (+)-norcamphor:implications of steric modification of the bicyclic framework on asymmetric sulfoxidation
Autori:	LATTANZI, Alessandra P. IANNECE SCETTRI, Arrigo mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2004
Rivista:	TETRAHEDRON-ASYMMETRY
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.
Handle:	http://hdl.handle.net/11386/1058689
Appare nelle tipologie:	1.1.2 Articolo su rivista con ISSN

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