A Facile Approach to α‐Keto Esters via Oxidative Esterification of α‐Amino Carbonyl Compounds
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DOI: 10.1002/ajoc.201900320
Abstract: A direct oxidative esterification of alpha-amino carbonyl compounds by two kinds of hydroperoxides, for the synthesis of alpha-keto esters has been developed. The reaction shows broad substrates scope and good functional group tolerance, even for… read more here.
Keywords: oxidative esterification; keto esters; amino carbonyl; carbonyl compounds ... See more keywords
Synthesis of Functionalized δ‐Hydroxy‐β‐keto Esters and Evaluation of Their Anti‐inflammatory Properties
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DOI: 10.1002/cbic.202200073
Abstract: δ‐Hydroxy‐β‐keto esters and δ,β‐dihydroxy esters are characteristic structural motifs of statin‐type natural products and drug candidates. Here, we describe the synthesis of functionalized δ‐hydroxy‐β‐keto esters in good yields and excellent enantioselectivities using Chan's diene and… read more here.
Keywords: synthesis functionalized; functionalized hydroxy; hydroxy keto; keto esters ... See more keywords
Improving Catalytic Activity and Reversing Enantio‐Specificity of ω‐Transaminase by Semi‐Rational Engineering en Route to Chiral Bulky β‐Amino Esters
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DOI: 10.1002/cctc.202100503
Abstract: The application of wild‐type ω‐transaminase was limited by steric hindrance towards bulky substrates, therefore improvement of the catalytic efficiency and stereoselectivity toward substrates with two bulky substituent adjacent to the carbonyl is of general interest.… read more here.
Keywords: bulky; keto esters; reversing enantio; transaminase ... See more keywords
Highly diastereoselective synthesis of trifluoromethyl containing spiro[pyrrolidin-3,2′-oxindoles] from N-2,2,2-trifluoroethylsubstituted isatin imines and β,γ-unsaturated α-keto esters
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron"
DOI: 10.1016/j.tet.2021.132112
Abstract: ABSTRACT Inspired by the chemistry and biology of fluorine-containing molecules and pyrrolidinyl spirooxindoles, herein we report a highly diastereoselective [3+2] cycloaddition reaction of β,γ-unsaturated α-keto esters and N-2,2,2-trifluoroethylisatin ketimines in the presence of the catalyst… read more here.
Keywords: spiro pyrrolidin; highly diastereoselective; keto esters; pyrrolidin oxindoles ... See more keywords
Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.
Sign Up to like & getrecommendations! Published in 2017 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.7b00263
Abstract: The unique role that stereochemistry plays in molecular recognition events continues to provide a driving force for synthesizing organic compounds in enantioenriched form. The tendency of enantioenriched organic compounds to revert to an entropically favored… read more here.
Keywords: hydrogenation; chemistry; keto esters; complex glycolates ... See more keywords
Cooperative Palladium/Brønsted Acid Catalysis toward the Highly Enantioselective Allenylation of β-Keto Esters.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00179
Abstract: We report the first enantioselective allenylation of Pd enolates enabled by cooperative Pd/Brønsted acid catalysis employing β-keto esters and propargyl alcohols. The enantioselectivity originates solely from an in-situ-generated chiral metal enolate in an open transition… read more here.
Keywords: acid catalysis; nsted acid; keto esters; enantioselective allenylation ... See more keywords
Recent advances in the transesterification of β-keto esters
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DOI: 10.1039/d1ra03513d
Abstract: This review summarises the many advances in the selective transesterification of β-keto esters, with a particular focus on the past 30 years. read more here.
Keywords: transesterification keto; advances transesterification; keto esters; recent advances ... See more keywords
Visible light-induced oxidative α-hydroxylation of β-dicarbonyl compounds catalyzed by ethylenediamine–copper(ii)
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DOI: 10.1039/d2ra07411g
Abstract: We have developed an efficient oxidative α-hydroxylation of β-keto esters with firstly using the structurally simple ethylenediamine–copper(ii) as a catalyst for β-keto esters activation and using visible light as the driving force for generating more… read more here.
Keywords: keto esters; ethylenediamine copper; oxidative hydroxylation; visible light ... See more keywords
I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage
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DOI: 10.1055/s-0036-1588833
Abstract: A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C… read more here.
Keywords: diketones alcohols; bond; tbhp promoted; keto esters ... See more keywords
Enantioselective Palladium-Catalyzed Decarboxylative Allylation of β-Keto Esters Assisted by a Thiourea
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DOI: 10.1055/s-0036-1590869
Abstract: Enantioselective intramolecular decarboxylative allylation of β-keto esters catalyzed by a palladium bis(phosphine)-thiourea complex is reported. This procedure is not only effective for β-keto esters, but also effective for β-keto amides. An intermolecular variant of the… read more here.
Keywords: decarboxylative allylation; keto esters; allylation keto; keto ... See more keywords
Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates
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DOI: 10.1055/s-0037-1612255
Abstract: Herein, we describe two practical methods to synthesize β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates promoted by BF3•Et2O in the presence of Ac2O or by Ti(OEt)4 under mild conditions. A variety of aromatic aldehydes… read more here.
Keywords: synthesis unsaturated; aldehydes pyruvates; unsaturated keto; keto esters ... See more keywords