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Stereocontrol in proline-catalyzed asymmetric amination: a comparative assessment of the role of enamine carboxylic acid and enamine carboxylate

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Title Stereocontrol in proline-catalyzed asymmetric amination: a comparative assessment of the role of enamine carboxylic acid and enamine carboxylate
 
Creator SHARMA, AK
SUNOJ, RB
 
Subject ALDOL REACTIONS
ALPHA-AMINATION
ORGANOCATALYSIS
OXAZOLIDINONES
PREDICTIONS
ALDEHYDES
ALCOHOLS
 
Description The transition state models in two mechanistically distinct pathways, involving (i) an enamine carboxylic acid (path-A, 4) and (ii) an enamine carboxylate (path-B, 8), in the proline-catalyzed asymmetric alpha-amination have been examined using DFT methods. The path-A predicts the correct product stereochemistry under base-free conditions while path-B accounts for reversal of configuration in the presence of a base.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2012-06-26T09:23:47Z
2012-06-26T09:23:47Z
2011
 
Type Article
 
Identifier CHEMICAL COMMUNICATIONS,47(20)5759-5761
1359-7345
http://dx.doi.org/10.1039/c1cc11063b
http://dspace.library.iitb.ac.in/jspui/handle/100/14278
 
Language English