ArticleAngewandte Chemie (International ed. in English)2016
Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Advances in Chiral Pincer Complexes: Insights and Applications in Catalytic Asymmetric Reactions.International journal of molecular sciences · 2024Review
- Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides.The Journal of organic chemistry · 2024Article
- Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles.Science advances · 2023Article
- Enantioseparation and racemization of 3-fluorooxindoles.Chirality · 2023Article
- Selective CspSynthesis · 2022Article
- Fluorine in metal-catalyzed asymmetric transformations: the lightest halogen causing a massive effect.Chemical science · 2022Review
- Article
- Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.Organic letters · 2021Article
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.Journal of the American Chemical Society · 2019Article
- Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.Angewandte Chemie (International ed. in English) · 2019Article
- Organocatalytic Decarboxylative Cyanomethylation of Difluoromethyl and Trifluoromethyl Ketones.Advanced synthesis & catalysis · 2018Article
- Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones.Angewandte Chemie (International ed. in English) · 2017Article
- Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.Journal of the American Chemical Society · 2017Article
- Catalytic asymmetric synthesis of CFChemical science · 2017Article
- Substrate-Controlled Product Divergence: Silver-Catalyzed Reaction of Trifluoromethyl Ketones with Terminal Alkynes.ACS omega · 2017Article
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2 authors.
Funding
Abstract
The asymmetric addition of terminal ynamides to trifluoromethyl ketones with a readily available chiral zinc catalyst gives CF3 -substituted tertiary propargylic alcohols in up to 99 % yield and 96 % ee. The exclusion of organozinc additives and base as well as the general synthetic utility of the products are key features of this reaction. The value of the β-hydroxy-β-trifluoromethyl ynamides is exemplified by selective transformations to chiral Z- and E-enamides, an amide, and N,O-ketene acetals. The highly regioselective hydration, stereoselective reduction, and hydroacyloxylation reactions proceed with high yields and without erosion of the ee value of the parent β-hydroxy ynamides.
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