Please use this identifier to cite or link to this item:
http://hdl.handle.net/11375/21629
Title: | Development of a Stereoselective Method for the Synthesis of β-Lactones |
Authors: | Anwar, Khandker |
Advisor: | Harrison, P. H. M. |
Department: | Chemistry |
Keywords: | Stereoselective;Synthesis;β-Lactones;natural products |
Publication Date: | May-2008 |
Abstract: | <p> β-Lactones are present in a number of biologically interesting natural products. They also have inherent reactivity due to their strained ring system and act as important synthetic intermediates. In this current work, we focus on the development of an efficient stereoselective route for the synthesis of β-lactones. A Tandem Evans-type Aldol Lactonization (TEAL) method was developed and various di- and tri-substituted β-lactones were successfully synthesized in a one pot process, using the lithium enolates of N-acetyl- (2-8) and N-propionyl- (2-20) thiazolidine-2-thione and a variety of ketones with moderate to good yields. Substitution of these N-acyl thiazolidine-2-thiones with chiral N-acetyl and N-propionyl thiazolidine-2-thiones (2-41 and 2-42 respectively) produced β-lactones with good enantioselectivity (up to 83% e.e.) and also showed an improvement of diastereoselectivity indicating the potential of the developed method. </p> |
URI: | http://hdl.handle.net/11375/21629 |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Anwar_Khandker_J_2008May_Masters.pdf | 2.17 MB | Adobe PDF | View/Open |
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