PEG-Solvent System for L-proline Catalyzed Wieland - Miescher Ketone Synthesis

ISSN: 2213-3380 (Online)
ISSN: 2213-3372 (Print)


Volume 1, 2 Issues, 2014






Current Organocatalysis

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Bimal K. Banik
Department of Chemistry
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The University of Texas-Pan American
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PEG-Solvent System for L-proline Catalyzed Wieland - Miescher Ketone Synthesis

Author(s): Vivek Srivastava

Affiliation: Natural Science: Chemistry, NIIT University, NH-8 Delhi-Jaipur Highway, Neemrana, Distt. Alwar, Rajasthan, India.

Abstract

The Wieland-Miescher ketone 4 serves as starting material for a wide range of natural product synthesis.This procedure represents one of the most efficient method for the synthesis of Wieland - Miescher ketone 4 with 1 mol% catalyst loading. PEG (400) mediated proline was used as catalyst to achieve the Wieland - Miescher ketone 4 via a nonselective conjugated addition reaction tailed by an enantioselective intermolecular Aldol condensation reaction of triketone 3 intermediate. All the reaction products were well characterized by sophisticated analytical techniques such as NMR, FTIR, HPLC, HRMS etc. Short reaction time, 8 times recycling of the catalyst, good yield (90%) and selectivity (99% ee) are the major outcomes of this proposed protocol.




Keywords: Amino acid, asymmetric synthesis, biologically active molecules, catalyst recycling, immobilized catalysis, ionic liquid, L-proline, PEG (400), organocatalysis, polymeric immobilization, wieland-miescher ketone.

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Article Details

Volume: 1
Issue Number: 1
First Page: 2
Last Page: 6
Page Count: 5
DOI: 10.2174/2213337201666140226000527
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