Work

Asymmetric Decarboxylative Protonation and Deuteration of Cyanoacetic Acids Using an Organometallic Proton Shuttle

Year: 2026

Type: article

Abstract: extrusion/protonation sequence in the decarboxylation of cyanoacetic acids and dictate its stereochemistry. While the amino motif in the ligand accommodates the proton, the nearby rhodium helps fix the orientation of the ketenimine intermediate for protonation via a dative bond. Furthermore, the decarboxylation pathway is compatible with H/D exchange using deuterated solvent, thus allowing an asymmetric decarboxylative deuteration. This method bridges the bulk production of cyanoacetates and their facile substitution with postdecarboxylation transformations of nitrile to access structurally diverse stereocenters and deuterated entities.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6c05281

Authors: Wei-Feng Zheng, Guozhen Wu, Min Hou, Ke Li, Xiaotian Qi, Zhongxing Huang

Institutions: State Key Laboratory of Synthetic Chemistry, University of Hong Kong, Wuhan University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500