Abstract

AbstractEnantioselective methylene insertion into prochiral cyclobutanones is described providing access to chiral β-substituted cyclopentanones as important structural motif in synthesis and natural products. Commercially available trimethylsilyl as well as other silyl diazomethanes act as one-carbon synthon and scandium triflate is found to be a potent Lewis acid catalyst. By using bis(oxazoline) ligands, enantioinduction is achieved for a number of β-substituted cyclopentanones including examples bearing all-carbon quaternary stereocentres.

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