NHCs Catalyzed Hydrophosphonylation ofα-Ketoesters andα-Trifluoromethyl Ketones

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NHCs Catalyzed Hydrophosphonylation of α-Ketoesters and α-Trifluoromethyl Ketones

N-Heterocyclic carbenes catalyzed hydrophosphonylation reaction of α-ketoesters and α-trifluoromethyl ketones was developed. Under the catalysis of 10 mol% IPr, α-ketoesters or α-trifluoromethyl ketones reacted with dialkyl phosphites to provide quaternary α-hydroxyphosphonates in good to excellent yield.

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Quinine-thiourea catalyzed enantioselective hydrophosphonylation of trifluoromethyl 2(1H)-quinazolinones.

An organocatalytic enantioselective addition reaction of cyclic ketoimines with phosphites has been developed for the first time. The process, catalyzed by Soós' quinine thiourea, affords synthetically and medicinally interesting enantioenriched trifluoromethyl dihydroquinazolinones in high yields and with high enantioselectivities.

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Enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones.

The catalytic asymmetric 1,2-addition of a series of arylboronic acids to 2,2,2-trifluoroacetophenones is described with high isolated yields (up to 96%) and good enantioselectivities (up to 83% ee) using a rhodium(I)/phosphoramidite catalyst.

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Highly enantioselective copper(I)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones.

The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(I)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic c...

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Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols.

Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording β-trifluoromethyl ketones in 65-73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric β-trifluoromethyl ketones in about 50% combined yield.

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ژورنال

عنوان ژورنال: The Scientific World Journal

سال: 2013

ISSN: 1537-744X

DOI: 10.1155/2013/890187