Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters.
Summary of "Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters."
Enantioselective Cu-catalyzed trifluoromethylation of β-ketoesters using commercially available trifluoromethylating reagents is reported. A number of α-CF(3) β-ketoesters are obtained with up to 99% ee. The trifluoromethylated products were then transformed diastereoselectively to α-CF(3) β-hydroxyesters with two adjacent quaternary stereocenters via a Grignard reaction.
Affiliation
Anorganisch-Chemisches Institut, Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Journal Details
This article was published in the following journal.
Name: Journal of the American Chemical Society
ISSN: 1520-5126
Pages: 10769-72
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22693950
- DOI: http://dx.doi.org/10.1021/ja3039773
Medical and Biotech [MESH] Definitions
Copper Radioisotopes
Unstable isotopes of copper that decay or disintegrate emitting radiation. Cu atoms with atomic weights 58-62, 64, and 66-68 are radioactive copper isotopes.
Menkes Kinky Hair Syndrome
An inherited disorder of copper metabolism transmitted as an X-linked trait and characterized by the infantile onset of HYPOTHERMIA, feeding difficulties, hypotonia, SEIZURES, bony deformities, pili torti (twisted hair), and severely impaired intellectual development. Defective copper transport across plasma and endoplasmic reticulum membranes results in copper being unavailable for the synthesis of several copper containing enzymes, including PROTEIN-LYSINE 6-OXIDASE; CERULOPLASMIN; and SUPEROXIDE DISMUTASE. Pathologic changes include defects in arterial elastin, neuronal loss, and gliosis. (From Menkes, Textbook of Child Neurology, 5th ed, p125)
Copper Sulfate
A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.
Hepatolenticular Degeneration
A rare autosomal recessive disease characterized by the deposition of copper in the BRAIN; LIVER; CORNEA; and other organs. It is caused by defects in the ATP7B gene encoding copper-transporting ATPase 2 (EC 3.6.3.4), also known as the Wilson disease protein. The overload of copper inevitably leads to progressive liver and neurological dysfunction such as LIVER CIRRHOSIS; TREMOR; ATAXIA and intellectual deterioration. Hepatic dysfunction may precede neurologic dysfunction by several years.
Amine Oxidase (copper-containing)
A group of enzymes including those oxidizing primary monoamines, diamines, and histamine. They are copper proteins, and, as their action depends on a carbonyl group, they are sensitive to inhibition by semicarbazide. EC 1.4.3.6.
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