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

ChemInform ◽  
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

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

2004 ◽  
Vol 57 (2) ◽  
pp. 135 ◽  
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]).

Trianions from .alpha.-hydroxy carboxylic acids

1978 ◽  
Vol 43 (20) ◽  
pp. 3963-3964 ◽  
Author(s):  
M. Newcomb ◽  
David E. Bergbreiter
Keyword(s):  
Carboxylic Acids ◽  
Hydroxy Carboxylic Acids

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

Synthesis ◽  
1996 ◽  
Vol 1996 (12) ◽  
pp. 1425-1427 ◽  
Author(s):  
Alan R. Katritzky ◽  
Dorin Toader ◽  
Linghong Xie
Keyword(s):  
Carboxylic Acids ◽  
Aldehydes And Ketones

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

2009 ◽  
Vol 44 (2) ◽  
pp. 252-259 ◽  
Author(s):  
Jason B. Bialecki ◽  
Frank U. Axe ◽  
Athula B. Attygalle
Keyword(s):  
Carboxylic Acids ◽  
Diagnostic Marker ◽  
Hydroxy Carboxylic Acids

Total Synthesis of Natural tert-Alkylamino Hydroxy Carboxylic Acids

ChemInform ◽  
2006 ◽  
Vol 37 (17) ◽  
Author(s):  
Sung Ho Kang ◽  
Suk Youn Kang ◽  
Hee-Seung Lee ◽  
Alan J. Buglass
Keyword(s):  
Total Synthesis ◽  
Carboxylic Acids ◽  
Hydroxy Carboxylic Acids
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