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Significance: The authors developed an oxazaborolidinium ion catalyzed asymmetric formal C–C bond insertion of diazo esters into aryl–CHO bonds to give functionalized acyclic all-carbon αquaternary aldehydes in good yields (up to 83%) and excellent enantioselectivities (up to 99%). The products were transformed into synthetically useful αand β-amino esters with ease. Comment: Contrary to the Roskamp reaction, the 1,2-aryl shift is preferred over the 1,2-hydride shift. It is the first catalytic asymmetric report of such a reaction. A variety of diazo esters and aldehydes were explored emphasizing synthetic flexibility. However, the regioselectivities are rather moderate (up to 88:12). Recently, Feng and coworkers reported a similar 1,2-aryl shift for the asymmetric homologation of α-keto esters (Angew. Chem. Int. Ed. 2013, 52, 10883). Applications: Selected examples:

Asymmetric Formal Insertion of Diazo Esters into Aryl–CHO Bonds