Synthesis of a renewable hydroperoxide from (+)-norcamphor: Influence of steric modifications of the bicyclic framework on asymmetric sulfoxidation

  • Lattanzi A
  • Iannece P
  • Scettri A
  • 5

    Readers

    Mendeley users who have this article in their library.
  • 24

    Citations

    Citations of this article.

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(Oi-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 stereoconvergent 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. © 2004 Elsevier Ltd. All rights reserved.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • Alessandra Lattanzi

  • Patrizia Iannece

  • Arrigo Scettri

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free