Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 40, Pages 12280-12284Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606571
Keywords
cycloaddition; heterocycles; N-heterocyclic carbene; organocatalysis; reaction mechanisms
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Funding
- Singapore National Research Foundation
- Ministry of Education of Singapore
- Nanyang Technological University (NTU, Singapore)
- China's Ministry of Education
- National Key program for Basic Research [2010CB 126105]
- Thousand Talent Plan
- National Natural Science Foundation of China [21132003, 21472028]
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An enantioselective beta-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 alpha,beta-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 beta(3)-amino-acid derivatives.
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