Access to Imidazolidin-2-ones via Azocarboxamide-Enabled Enantioselective 1,2-Diamination of Aldehyde.

The catalytic asymmetric synthesis of imidazolidin-2-ones has attracted widespread attention due to their diverse synthetic applications. Despite the great progress that has been made, the development of a straightforward, operationally simple protocol for the construction of chiral imidazolidin-2-ones from readily accessible starting materials remains highly desirable. Herein, we report an l-proline-catalyzed asymmetric 1,2-diamination of aldehydes with azocarboxamides (ACAs), which enables the efficient preparation of a broad range of chiral imidazolidin-2-ones in good yields and high enantioselectivities under mild reaction conditions. Furthermore, the feasibility of gram-scale synthesis and the successful late-stage transformation of the products into valuable hydantoin derivatives underscore the practical synthetic utility of this methodology in organic synthesis.