The stability of aromatic molecules limits the reactivity and, thereby, the synthetic utility of the resources. Dearomatization of aromatic molecules yields more reactive compounds with possible bonding sites at the sp2 carbon atoms. Previous work involving p-basic metal fragments binding aromatics in a dihapto fashion has successfully activated sp2 binding sites. d5 compounds give p-bases when reduced in the presence of aromatic molecules, forming complexes through p-backbonding. These established p-bases, however, had to be chirally resolved late in the reaction schemes in order to yield nonracemic products. A remedy to this issue would involve the use of p-basic metal fragments that include resolved chiral ligands which would control stereochemistry.Current work in our lab involves developing chiral C2-symmetric tetraamine ligands that preferentially complex with molybdenum or tungsten in a cis-a configuration. If the resulting d6 metal fragments are capable of binding aromatics, they may be able to limit subsequent addition reactions to a single enantioface. [(?3-Qnbp)W(NO)(CO)2]PF6 and (?3-MeImbp)Mo(CO)3 -were synthesized in 81.1% and 65.4% yields, respectively. A series of novel complexes involving the N,N'-(quinolyl-2-methyl)-2,2'-bispyrrolidine (Qnbp), Trans-N,N'-dimethyl-bis(3,4-dimethoxypyridyl-2-methyl)-1,2-cyclohexanediamine (DMO-picchxn), and N,N'-bis((1-methylimdazolyl)-2-methyl)-2,2'-bispyrrolidine (MeIm-bpy) ligands has been synthesized and characterized.

Synthesis and characterization of <i>C</i><sub>2</sub>-symmetric ligands for enantioselective dearomatization

247th National Meeting (2014)

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Synthesis and characterization of C2-symmetric ligands for enantioselective dearomatization

Synthesis and characterization of C₂-symmetric ligands for enantioselective dearomatization