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A practical method for the chemo- and diastereoselective allylation of α,β-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,β-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6.
This article was published in the following journal.
Name: Organic letters
A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to β-hydroxy ketones and α-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluor...
A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture a...
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Unstable isotopes of indium that decay or disintegrate emitting radiation. In atoms with atomic weights 106-112, 113m, 114, and 116-124 are radioactive indium isotopes.
Organic compounds containing an epoxide group and characterized by strength and thermosetting properties. Epoxy resins are often used as dental materials.
A genus of gram-negative, curved or straight rod-shaped bacteria, in the family ALTEROMONADACEAE. They are chemo-organotrophic, halophilic, and associated with cold marine habitats.
Treatment modality for DENTAL CARIES that uses manual excavation method and GLASS IONOMER CEMENTS. Because of its noninvasiveness and no need for expensive equipment and anesthesia it is promoted as an approach in places where dental care is not readily available.