Enantioselective syntheses of bicyclo[3.3.0]octan-3-one, bicyclo[3.2.1]octan-3-one and bicyclo[3.2.1]octan-2-one derivatives were accomplished by employing a chiron based approach, using intramolecular rhodium carbenoid C-H insertion, acid catalysed cyclisation of α-diazo ketone and intramolecular type II carbonyl ene reactions as key steps. © 2006 Elsevier Ltd. All rights reserved.