Copper-catalysed intramolecular C-H insertion reactions of alpha-diazo-beta-keto esters and alpha-diazo-beta-keto phosphonates are described, with moderate-to-good levels of enantioselectivity achieved for reactions employing the borate additive sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBARF). Notably, the first example of asymmetric induction reported to date for intramolecular C-H insertion of an alpha-diazo-beta-keto phosphonate is also described. (C) 2013 Elsevier Ltd. All rights reserved.