Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 314-325Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02808
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Funding
- MINECO
- FEDER [CTQ2017-84900-P]
- Spanish Government [RyC-2016-20187]
- Generalitat Valenciana
- Fondo Social Europeo [APOST/2016/139]
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The first enantioselective formal [3 + 2] cycloaddition between alpha-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Bronsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity.
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