Maguire, Anita R.; Shiely, Amy; Clarke, Leslie Ann; Flynn, Chris; Buckley, Aoife; Ford, Alan; Lawrence, Simon

2018

March

European Journal of Organic Chemistry

Substrate and catalyst effects in the enantioselective copper catalysed C-H insertion reactions of a-diazo-ß-oxo sulfones

Validated

()

Asymmetric C-H insertion Copper catalysis α-Diazocarbonyl compounds α-Diazo-β-oxo sulfones bis(oxazoline) ligands

Excellent enantioselectivities of up to 98% ee are achieved employing the copper‐bis(oxazoline)‐NaBARF catalyst system in the C‐H insertion reactions of α‐diazo‐β‐oxo sulfones. The influence of variation of the bis(oxazoline) ligand, copper salt, additive and substrate on both the efficiency and the enantioselectivities of these intramolecular C‐H insertion reactions has been explored. Optimum enantioselectivities are achieved with the phenyl and diphenyl ligands across the substrate series.

1099-0690

10.1002/ejoc.201800077