Abstract
The development of metal-catalyzed additions of nitrogen and oxygen moieties across alkenes to form saturated nitrogen and oxygen heterocycles is described herein. This chapter covers the most recent advances in osmium and palladium-catalyzed alkene oxidation and amination reactions and also summarizes the emerging areas of copper, iron, and gold-catalyzed alkene oxidations and aminations. In most examples, moderate to excellent levels of diastereoselectivity, either by stereospecific addition across the alkene or substrate-directed diastereocontrol, have been achieved. This enables the synthesis of nitrogen and oxygen-containing heterocycles with predictable control of stereogenic centers. In a few cases, asymmetric catalysis has been achieved, allowing for the synthesis of chiral nitrogen and oxygen-containing heterocycles from achiral substrates. In many of these oxidation reactions, use of pre-oxidized substrates or stoichiometric amounts of added oxidants are required to achieve the catalytic cycles, which frequently involve higher oxidation states of the metal catalysts.
Published Version
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