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

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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.

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Lattanzi, A., Iannece, P., & Scettri, A. (2004). Synthesis of a renewable hydroperoxide from (+)-norcamphor: Influence of steric modifications of the bicyclic framework on asymmetric sulfoxidation. Tetrahedron Asymmetry, 15(11), 1779–1785. https://doi.org/10.1016/j.tetasy.2004.04.027

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