Catalytic enantioselective proton transfer reactions

Abstract

Enantioselective proton transfer refers to the process of enantioselective introduction of protons to carbanions through the recognition of prochiral faces. Enantioselective proton transfer can easily construct tertiary carbon stereocenters, which widely exist in natural products and bioactive compounds. However, catalytic enantioselective proton transfer has been a long-lasting challenge in asymmetric synthesis because the proton is the smallest ion and the proton transfer process of active intermediates is generally fast with complicated pathways and strong background reaction. In recent years, a series of new catalysts and catalytic strategies have been developed for stereocontrol of proton transfer processes in various organic reactions. At the same time, more in-depth mechanism studies have revealed detailed information and regulations of proton transfer in catalytic reactions. This paper reviews the recent progress on catalytic enantioselective proton transfer reactions according reaction types. At the end of this paper, the stereocontrol strategies of catalytic proton transfer are classified and the prospects of this field are also presented.