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Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds pp 225–269Cite as

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

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

Abstract

In this section, the synthesis of saturated N- and O-heterocycles via formal cycloaddition is presented. The main focus is on metal-catalyzed reactions involving C–C or C–X σ bond cleavage in three- or four-membered rings. After a fast presentation of pioneering works, the important breakthroughs of the last two decades are presented. The section starts with reactions involving three-membered rings. Formal [3+2] cycloadditions of donor–acceptor-substituted cyclopropanes and methylenecyclopropanes with carbonyls and imines are important methods to access tetrahydrofuran and pyrrolidine heterocycles. Formal [3+3] cycloadditions have emerged more recently. On the other hand, reactions of epoxides and aziridines with carbon monoxide or cumulenes are now well-established methods to access heterocycles. These processes have been completed more recently with cycloaddition with olefins, carbonyls, and imines. The section ends with the emerging field of four-membered ring activation for cycloaddition with π systems.

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    Jerome Waser

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Waser, J. (2013). Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond. 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_108

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