Indium-Mediated Addition of 4-Bromocrotonic Acid to Aldehydes and Ketones—A Simple, High Yielding Route to α-Allyl-β-Hydroxy Carboxylic Acids

Michael C. Bowyer; Charles M. Gordon; Sarah K. Leitch; Adam McCluskey; Craig Ritchie

doi:10.1071/ch03212

Indium-Mediated Addition of 4-Bromocrotonic Acid to Aldehydes and Ketones—A Simple, High Yielding Route to α-Allyl-β-Hydroxy Carboxylic Acids

Australian Journal of Chemistry ◽

10.1071/ch03212 ◽

2004 ◽

Vol 57 (2) ◽

pp. 135 ◽

Cited By ~ 7

Author(s):

Michael C. Bowyer ◽

Charles M. Gordon ◽

Sarah K. Leitch ◽

Adam McCluskey ◽

Craig Ritchie

Keyword(s):

Ionic Liquid ◽

Carboxylic Acids ◽

Simple Procedure ◽

Effect Of Solvent ◽

Reaction Proceeds ◽

Aldehydes And Ketones ◽

Hydroxy Carboxylic Acids ◽

Ethanol Ethanol

We report a simple procedure for the indium-mediated addition of 4-bromocrotonic acid to a variety of aldehydes and ketones. In all instances the reaction proceeds exclusively with α-addition and typically in moderate to good yields (42–100%). The effect of solvent is minimal allowing a wide choice of conditions (methanol, ethanol, ethanol/water, water, tetrahydrofuran, and the ionic liquid [bmIm][BF4]).

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Efficient and convenient oxidation of aldehydes and ketones to carboxylic acids and esters with H2O2 catalyzed by Co4HP2Mo15V3O62 in ionic liquid [TEBSA][BF4]

RSC Advances ◽

10.1039/c5ra02234g ◽

2015 ◽

Vol 5 (32) ◽

pp. 24936-24943 ◽

Cited By ~ 7

Author(s):

Yu-Lin Hu ◽

De-Jiang Li ◽

Dong-Sheng Li

Keyword(s):

Ionic Liquid ◽

Carboxylic Acids ◽

Aldehydes And Ketones

A simple, efficient, and eco-friendly procedure for the oxidation of aldehydes and ketones to carboxylic acids and esters with H2O2 catalyzed by Co4HP2Mo15V3O62 in ionic liquid [TEBSA][BF4] has been developed.

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ChemInform Abstract: Efficient and Convenient Oxidation of Aldehydes and Ketones to Carboxylic Acids and Esters with H2O2Catalyzed by Co4HP2Mo15V3O62in Ionic Liquid [TEBSA][BF4].

ChemInform ◽

10.1002/chin.201530047 ◽

2015 ◽

Vol 46 (30) ◽

pp. no-no

Author(s):

Yu-Lin Hu ◽

De-Jiang Li ◽

Dong-Sheng Li

Keyword(s):

Ionic Liquid ◽

Carboxylic Acids ◽

Aldehydes And Ketones

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Indium-Mediated Addition of 4-Bromocrotonic Acid to Aldehydes and Ketones — A Simple, High-Yielding Route to α-Allyl-β-hydroxy Carboxylic Acids.

ChemInform ◽

10.1002/chin.200424090 ◽

2004 ◽

Vol 35 (24) ◽

Author(s):

Michael C. Bowyer ◽

Charles M. Gordon ◽

Sarah K. Leith ◽

Adam McCluskey ◽

Craig Ritchie

Keyword(s):

Carboxylic Acids ◽

Aldehydes And Ketones ◽

Hydroxy Carboxylic Acids

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Synthesis of 13 C‐Labelled ω‐Hydroxy Carboxylic Acids of the General Formula HO 2 13 C‐(CH 2 ) n ‐CH 2 OH or HO 2 C‐(CH 2 ) n ‐ 13 CH 2 OH (n = 12, 16, 20, 28)

Journal of Labelled Compounds and Radiopharmaceuticals ◽

10.1002/jlcr.3931 ◽

2021 ◽

Author(s):

Carina Schink ◽

Sandra Spielvogel ◽

Wolfgang Imhof

Keyword(s):

General Formula ◽

Carboxylic Acids ◽

Hydroxy Carboxylic Acids

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Application of ion-exclusion chromatography to alkaline pulping liquors; separation of hydroxy carboxylic acids from inorganic solids

Journal of Chemical Technology & Biotechnology ◽

10.1002/jctb.280510208 ◽

2007 ◽

Vol 51 (2) ◽

pp. 225-233 ◽

Cited By ~ 20

Author(s):

Raimo Alén ◽

Eero Sjöström ◽

Seija Suominen

Keyword(s):

Carboxylic Acids ◽

Inorganic Solids ◽

Alkaline Pulping ◽

Ion Exclusion Chromatography ◽

Ion Exclusion ◽

Exclusion Chromatography ◽

Hydroxy Carboxylic Acids ◽

Pulping Liquors

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Trianions from .alpha.-hydroxy carboxylic acids

The Journal of Organic Chemistry ◽

10.1021/jo00414a036 ◽

1978 ◽

Vol 43 (20) ◽

pp. 3963-3964 ◽

Cited By ~ 8

Author(s):

M. Newcomb ◽

David E. Bergbreiter

Keyword(s):

Carboxylic Acids ◽

Hydroxy Carboxylic Acids

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Efficient Transformations of Aldehydes and Ketones into One-Carbon Homologated Carboxylic Acids

Synthesis ◽

10.1055/s-1996-4424 ◽

1996 ◽

Vol 1996 (12) ◽

pp. 1425-1427 ◽

Cited By ~ 12

Author(s):

Alan R. Katritzky ◽

Dorin Toader ◽

Linghong Xie

Keyword(s):

Carboxylic Acids ◽

Aldehydes And Ketones

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ChemInform Abstract: Catalytic Conversion of β-Hydroxy Carboxylic Acids to Olefins by Tungsten(VI) Complexes: A New Acyl Group Transfer Catalyst.

ChemInform ◽

10.1002/chin.199113092 ◽

2010 ◽

Vol 22 (13) ◽

pp. no-no

Author(s):

T. TANZAWA ◽

J. SCHWARTZ

Keyword(s):

Carboxylic Acids ◽

Catalytic Conversion ◽

Group Transfer ◽

Hydroxy Carboxylic Acids

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Boron acid complexation reactions with polyols and α-hydroxy carboxylic acids: Equilibria, reaction mechanisms, saccharide recognition

Inorganica Chimica Acta ◽

10.1016/j.ica.2017.08.003 ◽

2017 ◽

Vol 467 ◽

pp. 194-197 ◽

Cited By ~ 6

Author(s):

Richard Pizer

Keyword(s):

Carboxylic Acids ◽

Reaction Mechanisms ◽

Boron Acid ◽

Hydroxy Carboxylic Acids ◽

Complexation Reactions ◽

Saccharide Recognition

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Hydroxycarbonyl anion (m/z45), a diagnostic marker for α-hydroxy carboxylic acids

Journal of Mass Spectrometry ◽

10.1002/jms.1504 ◽

2009 ◽

Vol 44 (2) ◽

pp. 252-259 ◽

Cited By ~ 14

Author(s):

Jason B. Bialecki ◽

Frank U. Axe ◽

Athula B. Attygalle

Keyword(s):

Carboxylic Acids ◽

Diagnostic Marker ◽

Hydroxy Carboxylic Acids

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