Abstract |
The first copper-catalyzed ring-opening electrophilic trifluoromethylation and trifluoromethylthiolation of cyclopropanols to form Csp3-CF3 and Csp3-SCF3 bonds have been realized. These transformations are efficient for the synthesis of β-CF3- and β-SCF3-substituted carbonyl compounds that are otherwise challenging to access. The reaction conditions are mild and tolerate a wide range of functional groups. Application to a concise synthesis of LY2409021, a glucagon receptor antagonist that is used in clinical trials for type 2 diabetes mellitus, is reported as well.
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Authors | Yong Li, Zhishi Ye, Tabitha M Bellman, Teng Chi, Mingji Dai |
Journal | Organic letters
(Org Lett)
Vol. 17
Issue 9
Pg. 2186-9
(May 01 2015)
ISSN: 1523-7052 [Electronic] United States |
PMID | 25885795
(Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
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Chemical References |
- Alkenes
- Biphenyl Compounds
- Ethers, Cyclic
- Hydrocarbons, Fluorinated
- Iodides
- Receptors, Glucagon
- cyclopropanol
- adomeglivant
- Copper
- cuprous iodide
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Topics |
- Alkenes
(chemistry)
- Biphenyl Compounds
(chemical synthesis, chemistry, pharmacology)
- Catalysis
- Copper
(chemistry)
- Diabetes Mellitus, Type 2
(drug therapy)
- Ethers, Cyclic
(chemistry)
- Hydrocarbons, Fluorinated
(chemical synthesis, chemistry, pharmacology)
- Iodides
(chemistry)
- Molecular Structure
- Receptors, Glucagon
(antagonists & inhibitors)
- Stereoisomerism
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