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
2004-01-01

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.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/1058689
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 21
social impact