Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 691, Issue 10, Pages 2072-2082Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2005.10.051
Keywords
optically pure alkyl hydroperoxides; metal-catalyzed oxidations; kinetic resolution; enantiomerically enriched sulfoxides; enantiomerically enriched epoxy alcohols; diastereoselective oxidations
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Metal-catalyzed asymmetric oxidations which rely on the use of commercially available t-butyl (TBHP) or cumyl hydroperoxides (CHP) and enantiopure ligands represent the majority of protocols reported to obtain enantiomerically enriched valuable compounds such as epoxides, sulfoxides, diols, etc. Herein, we review our recent results on the complementary and less studied oxidative approach based on the use of optically pure alkyl hydroperoxides as oxygen and chirality source. The synthetic sequence to enantiopure furyl hydroperoxides, easily accessible from ketones of the chiral pool is firstly described. Examples of metal-catalyzed asymmetric oxidations using these compounds for the production of enantiomerically enriched sulfoxides and epoxy alcohols are shown. The entire protocol is made more advantageous by recovering the optically pure alcohols during the purification procedure and recycling them for the one-step synthesis of the hydroperoxides. (c) 2005 Elsevier B.V. All rights reserved.
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