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Current Organocatalysis


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

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

Author(s): Vivek Srivastava

Volume 1 , Issue 1 , 2014

Page: [2 - 6] Pages: 5

DOI: 10.2174/2213337201666140226000527


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.

Graphical Abstract

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