2.2 Metal-Catalyzed Cyclopropanation

L. Garve; D. B. Werz

Abstract

This chapter describes the most important metal-catalyzed methods to generate cyclopropanes, the smallest class of cycloalkanes. In the past fifty years, the use of metals in combination with chiral ligands for diastereo- and enantiodiscrimination in cyclopropane synthesis has been intensively studied. Two main approaches have emerged. Utilizing carbenes in the form of metal–carbene complexes has led to a renaissance of three-membered-rings in organic synthesis. In another approach, metal cations such as gold(I) and platinum(II) interact with alkynes, forming novel cyclopropane motifs. Finally, further metal-catalyzed cyclopropanations are mentioned.

Key words

cyclopropanes - three-membered rings - metal-catalyzed cyclopropanation - asymmetric cyclopropanation - carbenes - metal–carbene complexes - Kulinkovich cyclopropanation - enynes - copper - rhodium - cobalt - iridium - ruthenium - iron - palladium - gold - platinum - titanium - bicyclic molecules

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