Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 20, Pages 4790-4796Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900831
Keywords
organocatalysis; enantioselective azidation; squaramide; aza-Michael; direct activation
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Funding
- Spanish Government [CTQ2015-64561-R, RTI2018-095038-B I00]
- Comunidad de Madrid
- European Structural Funds [S2018/NMT-4367]
- University of Salerno
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An enantioselective organocatalytic conjugate azidation of alpha,beta-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.
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