Wolfbeis, Eds., Proceedings of the NATO Advanced Research Workshop on Syntheses, Optical Properties and Applications of Near Infrared (NIR) Dyes in High Technology Fields.
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Chapter 2 - Synthesis of Acetylenic CF3-ketones
Chapter 3 - The Application of a,b-Unsaturated Trifluoromethylketones in Synthesis
Direct Synthesis of a Trifluoromethyl Copper Reagent …
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A highly enantioselective and practical synthesis of the HIV-1 reverse transcriptase inhibitor efavirenz (1) is described. The synthesis proceeds in 62% overall yield in seven steps from 4-chloroaniline (6) to give efavirenz (1) in excellent chemical and optical purity. A novel, enantioselective addition of Li-cyclopropyl acetylide (4a) to -methoxybenzyl-protected ketoaniline 3a mediated by (1,2)--pyrrolidinylnorephedrine lithium alkoxide (5a) establishes the stereogenic center in the target with a remarkable level of stereocontrol.
Alcohol synthesis by 1,2-addition - Organic chemistry
Sloop, Matthew Churley, Alejandro Guzman, Samantha Moseley, Stephanie Stalker, Jonathan Weyand, Jonathan Yi, Synthesis and Reactivity of Fluorinated Cyclic Ketones: Initial Findings, , Vol.
Practical Asymmetric Synthesis of Efavirenz (DMP …
AB - Background: Since trifluoromethyl-containing compounds have found diverse applications in the fields of pharmaceuticals and agrochemicals, facile and selective synthetic methods for trifluoromethyl-substituted compounds are an essential tool for advanced medicinal chemistry. Now that diverse synthetic transformations of carbon-carbon triple bonds are available, 3,3,3-trifluoropropynyl-substituted compounds serve as versatile building blocks for target molecules containing trifluoromethyl groups. Thus, novel synthetic methods and reagents for incorporation of a 3,3,3-trifluoropropynyl group into an organic compound have been the major concern in exploration and modification of fluorine-based biologically active substances. Results & discussion: We report a preparative method of 3,3,3-trifluoropropynyllithium and its reaction with electrophiles including aldehydes, ketones, trimethoxyborane, chlorosilanes and chlorostannanes in detail. Palladium-catalyzed synthetic reactions of the carbonyl adducts and the trifluoromethyl-containing metalloid reagents are also demonstrated, which provide simple synthetic methods of trifluoromethylated allenes, arylacetylenes and enynes. The synthetic transformations presented here expand the repertoire of trifluoromethylated compounds available for medicinal scientists and contribute to the advance of future medicinal chemistry.
Synthesis of N-substituted 6-trifluoromethyl-1,3 …
A method has been developed for the synthesis of α-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers with an electrophilic trifluoromethylating agent, which produces a trifluoromethyl radical.