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
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Creator |
SHARMA, AK
SUNOJ, RB |
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Subject |
ALDOL REACTIONS
ALPHA-AMINATION ORGANOCATALYSIS OXAZOLIDINONES PREDICTIONS ALDEHYDES ALCOHOLS |
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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.
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Publisher |
ROYAL SOC CHEMISTRY
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Date |
2012-06-26T09:23:47Z
2012-06-26T09:23:47Z 2011 |
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Type |
Article
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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 |
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Language |
English
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