Abstract
Functionalized α-tertiary and -quaternary 2-arylcycloalkanones
are rapidly accessed by scandium(III) triflate-catalyzed diazoalkane-carbonyl
homologations. Recent developments have allowed for carbon insertion
reactions to be performed with catalyst loadings as low as 0.5 mol% on
scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline)
based ligands with scandium triflate allows access to arylated medium
ring carbocycles with enantioselectivities up to 98:2 er and >98% yield.
The formal C-C insertion of aryldiazomethanes
into unsubstituted cycloalkanones provides a single-step solution
to the ongoing challenge of α-arylation.
Key words
diazo compounds - scandium - asymmetric catalysis - ring expansion - arylation
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