Asymmetric decarboxylative protonation enabled by an anchoring group that enhances noncovalent interactions

Abstract

Stereoselective protonation is one of the grand challenges of asymmetric catalysis. Given its small size and high rate of transfer, the face selective delivery of a proton to planar intermediates is hard to control yet can unlock previously obscure asymmetric transformations. Particularly, when coupled with a preceding decarboxylation, enantioselective protonation can convert the abundant acid feedstocks to structurally diverse chiral molecules. Here, an anchoring group strategy was demonstrated as a potential alternative and supplement to the conventional structural modification of catalysts by creating additional catalyst-substrate interactions. We show that a tailored benzamide group in aminomalonic acids can help build a coordinated network of noncovalent interactions (NCIs), including hydrogen bonds, π-π interaction, and dispersion forces with a chiral acid catalyst, staging an enantioselective decarboxylative protonation togive α-amino acids.

Jingdan Chen 陈敬丹

Chemistry Undergraduate

My previous research concentrate on computational chemistry, while I would like to contribute to general data-driven chemical research.