期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 361, 期 20, 页码 4790-4796出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900831
关键词
organocatalysis; enantioselective azidation; squaramide; aza-Michael; direct activation
资金
- Spanish Government [CTQ2015-64561-R, RTI2018-095038-B I00]
- Comunidad de Madrid
- European Structural Funds [S2018/NMT-4367]
- University of Salerno
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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