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Aminomethylation of Enals through Carbene and Acid Cooperative Catalysis: Concise Access to β 2 ‐Amino Acids
Author(s) -
Xu Jianfeng,
Chen Xingkuan,
Wang Ming,
Zheng Pengcheng,
Song BaoAn,
Chi Yonggui Robin
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201412132
Subject(s) - iminium , carbene , chemistry , nucleophile , electrophile , organocatalysis , catalysis , amino acid , brønsted–lowry acid–base theory , combinatorial chemistry , conjugated system , formaldehyde , methanol , organic chemistry , medicinal chemistry , enantioselective synthesis , polymer , biochemistry
A convergent, organocatalytic asymmetric aminomethylation of α,β‐unsaturated aldehydes by N‐heterocyclic carbene (NHC) and (in situ generated) Brønsted 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 β 2 ‐amino acids bearing various substituents.