Enantioselective tandem Michael–aldol and oxidative Michael–aldol approaches have been achieved for the formation of diversely substituted cyclohexanes in total regio-, diastereo- and enantioselective fashion. The presence of nitro, hydroxy and keto groups in the product provides a wide scope for further structural transformations. Furthermore, the utility of the catalytic process is demonstrated in the context of enantioselective formal synthesis of ABT-341, a DPP4 inhibitor. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim