Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 22, Pages 11330-11338Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01829
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Funding
- National Natural Science Foundation of China [21072056, 21272067]
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Cinchona alkaloid squaramide can effectively catalyze the asymmetric Michael addition of alpha-aryl isocyanoacetates to beta-trifluoromethylated enones, affording the corresponding adducts, with an adjacent chiral tertiary carbon center bearing a CF3 group and a quaternary carbon center in moderate to good yields along with excellent stereo-selectivities. The adduct can be easily transformed into biologically attractive chiral beta-trifluoromethylated pyrroline carboxylate in high yield via an isocyano group hydrolysis/cyclization/dehydration cascade reaction by treating with acid. The one-pot enantioselective Michael addition/isocyano group hydrolysis/cyclization/dehydration sequential protocol has also been investigated.
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