<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> / Thesis / Master of Science (MSc)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/21629 |
| Date | 05 1900 |
| Creators | Anwar, Khandker |
| Contributors | Harrison, P. H. M., Chemistry |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
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