Chiral organometallic complexes are one of the most versatile and efficient asymmetric catalysts. In particular, asymmetric organometallic catalysts bearing chiral ligands have been widely used in chiral transformations. Other asymmetric organometallic catalysts, where the chiral element is located only at the metal center, have been rarely reported. In those complexes, the chiral metal center interacts directly with the substrate, and thus may achieve efficient chiral induction. In 2013, we reported the first metallapentalyne framework, which can be viewed as a 7 carbon chain coordinated to a metal via three metal-carbon bonds. With the extension of the carbon chain, a series of novel metal bridgehead polycyclic frameworks (from a 7C framework to a 12C framework) named as carbolongs were constructed. The strong chelation and the remarkable aromaticity make carbolong complexes quite stable. Therefore, starting from carbolong complexes, we synthesized a series of chiral-only-at-metal catalysts through chiral resolution and modification, and successfully applied them to the nitro-Mannich and Friedel-Crafts reactions with high stereoselectivity.

Synthesis and Application of Chiral-Only-at-Metal Carbolong Complexes

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