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Enantioselective Nucleophilic β‐Carbon‐Atom Amination of Enals: Carbene‐Catalyzed Formal [3+2] Reactions |
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| Authors: | Xingxing Wu Bin Liu Yuexia Zhang Martin Jeret Honglin Wang Pengcheng Zheng Prof Song Yang Prof Bao‐An Song Prof Dr Yonggui Robin Chi |
| Institution: | 1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, Singapore;2. Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China |
| Abstract: | An enantioselective β‐carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N‐heterocyclic‐carbene‐bound α,β‐unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3‐amino‐acid derivatives. |
| Keywords: | cycloaddition heterocycles N-heterocyclic carbene organocatalysis reaction mechanisms |