<p>Developing a unified method that can construct almost all types of chiral centres has been an unrealized aspiration for synthetic chemists. Boron-mediated homologation can generate versatile boron-substituted stereocentres via asymmetric carbenoid insertion, potentially leading to diverse chiral centres. However, limitations of the current methods make it challenging to incorporate a wide range of functionalized carbenoids with high stereochemical control. Here we report an enantioconvergent approach for direct insertion of various carbon-, oxygen-, nitrogen-, sulfur- and silicon-substituted carbenoids into carbon–boron bonds of readily available boronic acid derivatives, which can then be transformed into a wide range of tertiary chiral centres. Excellent stereoselectivity was achieved and enabled by a class of chiral oxazaborolidines derived from inexpensive α-amino esters. Computational studies revealed that the non-C2-symmetric oxazaborolidine features a puckered geometry and the cooperative effects of multiple substituents create an asymmetric environment for effective enantioinduction. This method is scalable, and each chiral centre can be independently controlled by the chiral oxazaborolidine without being influenced by nearby stereocentres. In addition to forming singular chiral centres, iterative operations of this asymmetric homologation simplify syntheses of complex molecules with multiple stereocentres.</p><p></p>