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Title: Aminomethylation of enals through carbene and acid cooperative catalysis : concise access to β2-amino acids
Authors: Chi, Robin Yonggui
Xu, Jianfeng
Chen, Xingkuan
Wang, Ming
Zheng, Pengcheng
Song, Bao-An
Keywords: DRNTU::Science::Chemistry::Physical chemistry::Catalysis
Issue Date: 2015
Source: Xu, J., Chen, X., Wang, M., Zheng, P., Song, B. A.,& Chi, Y. R. (2015). Aminomethylation of enals through carbene and acid cooperative catalysis : concise access to β2-amino acids. Angewandte chemie International edition, 54(17), 5161-5165.
Series/Report no.: Angewandte chemie International edition
Abstract: 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 β2-amino acids bearing various substituents.
ISSN: 1433-7851
DOI: 10.1002/anie.201412132
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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