A convenient transformation of alkynes to α-hydroxy-α-CF3-γ-ketoester derivatives via H3PO4-catalyzed tandem hydration and aldol condensation

Wang, Jiali; Yao, Jun; Jia, Chunqi; Hu, Dandan; Chen, Yunhua; Song, Jian; Zhang, Junqi; Ren, Hongjun

doi:10.1039/d2gc01199a

Cited by 5 publications

(1 citation statement)

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“…However, the obtained 7a could not react with trifluoroacetaldehyde hydrate 2a or ethyl trifluoropyruvate 2b under standard conditions to afford the corresponding products (Scheme ), implying that C–H bond trifluoromethyl alkylation may occur before chromone annulation. According to the above experiments and previous reports, , a plausible mechanism for this metal-free tandem reaction was proposed (Scheme ). First, trifluoroacetaldehyde hydrate 2a has a propensity to form its dehydrated ketoaldehyde 2a′ , which might provide a driving force for the occurrence of the aldol reaction with o -hydroxyphenyl enaminone 1a , delivering intermediate A .…”

Section: Resultsmentioning

confidence: 62%

A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives

et al. 2023

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Herein, we present a practical strategy for the direct construction of structurally diverse trifluoromethyl carbinolcontaining compounds, especially CF 3 -substituted tertiary alcohol with chromone derivatives from easily available o-hydroxyaryl enaminones and trifluoroacetaldehyde/ketone derivatives under metal-free conditions. This reaction features a broad substrate scope with good yields and is easily scaled up. Notably, a one-pot in two-steps reaction of obtained products with amidines is also developed to provide a series of multi-substituted pyrimidine derivatives bearing two unique hydroxyls and one trifluoromethyl containing functional units.

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Section: Resultsmentioning

confidence: 62%

A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives

et al. 2023

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Photoinduced Metal- and Photosensitizer-Free Decarbonylative C–H Alkylation of Cyclic Sulfamidate Imines

Fang,

Yu,

et al. 2023

J. Org. Chem.

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Catalytic Enantioselective Aldol Reactions of Pyruvates as Nucleophiles with Chlorinated and Fluorinated Aldehydes and Ketones

Mondal,

Tanaka

2024

J. Org. Chem.

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Reactions of pyruvates as nucleophiles under catalytic conditions are difficult to control without the use of enzymes as catalysts. Here, enantioselective aldol reactions of pyruvates with chlorinated and fluorinated aldehydes and ketones under organocatalytic conditions, in which pyruvates act as nucleophiles, are reported. Based on analyses of self-aldol reactions of pyruvates in the presence of model catalysts, catalysts of the desired cross aldol reactions were developed. Using the primary amine-derived catalyst, the desired aldol products, i.e., γ-chlorinated alkyl or γ-fluorinated alkyl group-substituted γ-hydroxy α-ketoesters, were obtained in good to high yields with high enantioselectivities.

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A convenient transformation of alkynes to α-hydroxy-α-CF₃-γ-ketoester derivatives via H₃PO₄-catalyzed tandem hydration and aldol condensation

Abstract: A robust metal-free catalytic strategy for the rapid construction of valuable α-Hydroxy-α-CF3-γ-ketoester skeleton with cheap and easily available stock chemicals alkynes and trifluoropyruvate as the starting material is described. This...

Cited by 5 publications

References 44 publications

A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives

A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives

Photoinduced Metal- and Photosensitizer-Free Decarbonylative C–H Alkylation of Cyclic Sulfamidate Imines

Catalytic Enantioselective Aldol Reactions of Pyruvates as Nucleophiles with Chlorinated and Fluorinated Aldehydes and Ketones

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