IISER Kolkata ePrints Repository

Organocatalytic Aldol Condensation of Thiazolidinedione Derivatives

Chauhan, Ajay (2011) Organocatalytic Aldol Condensation of Thiazolidinedione Derivatives. Masters thesis, Indian Institute of Science Education and Research, Kolkata.

[img] PDF (MS-Thesis of Ajay Chauhan(09IP04)) - Submitted Version
Restricted to Repository staff only

Download (4Mb)

    Abstract

    Recent years have witnessed an explosive growth in the field of organocatalysis, especially in asymmetric enamine and iminium catalysis. The use of simple amino acids as catalyst for the intermolecular direct aldol reaction at the beginning of this century became a true milestone in the growth of organocatalysis as a useful synthetic strategy. Since then, a plethora of new organocatalytic systems have been developed allowing to reach extraordinary levels of efficiencies, widening the scope of substrates used. Several modifications have been introduced to overcome some of the initial drawbacks, such as long reaction times, high catalyst loading, excess of reagents, etc., improving the expectations for their use in large scale synthesis. The acquired knowledge in this area has allowed the application of this strategy to be used in the synthesis of natural products. Thiazolidinedione units are important structural subunits present in many natural products and biologically active compounds. In this thesis we describe aldol condensation of N-substituted-2,4-thiazolidinedione derivatives 1 with a variety of aromatic aldehydes 2 using different amino acid catlysts 3. We have investigated the effects of solvent and different amino acids on the reaction to achieve the corresponding thiazolidine containing b-hydroxy carbonyl products 4 and 5 in high yield and diasterioselectivity. Amino acids catalysts 3 efficiently catalyzed aldol reaction between thiazolidinediones 1 and a variety of aromatic aldehydes 2 to give the corresponding syn and anti hydroxy thiazolidinediones 4 and 5 in good to excellent yields and moderate distreoselectivity.

    Item Type: Thesis (Masters)
    Additional Information: Under Supervision of Dr. Jyotirmayee Dash
    Uncontrolled Keywords: Organocatalysis; Aldehydes; Aldol Reaction; Stereoselectivity; Thiazolidinediones
    Subjects: Q Science > QD Chemistry
    Divisions: Faculty of Engineering, Science and Mathematics > School of Chemistry
    Depositing User: IISER Kolkata Librarian
    Date Deposited: 03 Jun 2011 13:02
    Last Modified: 27 May 2013 14:16
    URI: http://eprints.iiserkol.ac.in/id/eprint/12

    Actions (login required)

    View Item