Highly Position- and Enantioselective Catalytic Epoxidation of Polyolefins Mediated by a Chiral Mn Complex, Including a One-Step Conversion of Squalene to the (<i>S</i>)-2,3-Epoxide, a Precursor of Natural Steroids and Terpenoids
G. Sudhakar Reddy, E. J. Corey
Abstract
Reported herein is the synthesis of a novel chiral dicarboxylic ligand for Mn(II) and the application of the Mn complex to the highly enantio- and position-selective epoxidation of C═C under mild conditions, even with polyolefinic substrates. A stereomechanistic basis for asymmetric induction is suggested.
Topics & Concepts
ChemistryEnantioselective synthesisEpoxideSqualeneCatalysisOrganic chemistryPlant biochemistry and biosynthesisCholesterol and Lipid MetabolismMetal-Catalyzed Oxygenation Mechanisms