Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 19, Pages 9728-9739Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01820
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Funding
- Royal Society
- European Research Council under the European Union [279850]
- Engineering and Physical Sciences Research Council [EP/K039210/1, EP/K031252/1] Funding Source: researchfish
- EPSRC [EP/K039210/1, EP/K031252/1] Funding Source: UKRI
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alpha,beta-Unsaturated trichloromethyl ketones are suitable a alpha,beta-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels Alder reactions with azolium enolates generated from alpha-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).
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