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Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Diamination, Aminoalkoxylation, or Dialkoxylation Reactions

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Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 32))

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.

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  1. Department of Chemistry, The State University of New York at Buffalo, Buffalo, NY, 14260, USA

    Sherry R. Chemler & David A. Copeland

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Correspondence to Sherry R. Chemler .

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  1. Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA

    John P. Wolfe

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Chemler, S.R., Copeland, D.A. (2013). Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Diamination, Aminoalkoxylation, or Dialkoxylation Reactions. In: Wolfe, J. (eds) Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds. Topics in Heterocyclic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2013_104

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