1026021-17-9Relevant articles and documents
Aminomethylation of enals through carbene and acid cooperative catalysis: Concise access to β2-amino acids
Xu, Jianfeng,Chen, Xingkuan,Wang, Ming,Zheng, Pengcheng,Song, Bao-An,Chi, Yonggui Robin
, p. 5161 - 5165 (2015)
A convergent, organocatalytic asymmetric aminomethylation of α,β-unsaturated aldehydes by N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperative catalysis is disclosed. The catalytically generated conjugated acid from the base plays dual roles in promoting the formation of azolium enolate intermediate, formaldehyde-derived iminium ion (as an electrophilic reactant), and methanol (as a nucleophilic reactant). This redox-neutral strategy is suitable for the scalable synthesis of enantiomerically enriched β2-amino acids bearing various substituents. Harmonious cooperation: An N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperatively catalyze the aminomethylation of α,β-unsaturated aldehydes. This cooperative catalytic reaction provides a redox neutral strategy for quick access to β2-amino esters in an enantioselective manner.