Aminomethylation of Enals through Carbene and Acid Cooperative Catalysis: Concise Access to β2‐Amino Acids |
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| Authors: | Dr. Jianfeng Xu Xingkuan Chen Dr. Ming Wang Pengcheng Zheng Bao‐An Song Prof. Dr. Yonggui Robin Chi |
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| Affiliation: | 1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore);2. Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025 (China) |
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| 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. |
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| Keywords: | amino acids asymmetric synthesis Brø nsted acid N‐heterocyclic carbenes organocatalysis |
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