The racemic homoallylic and homopropargylic alcohol derivatives were
resolved by applying chemoenzymatic method using various lipase type enzymes
i.e., PS-C II, Lipozyme, CAL-B. The enantiomeric excess values of the resultant
alcohols were determined by HPLC. These enantiomerically enriched homoallylic
and homopropargylic alcohols were subjected to N-propargylation and N-allylation,
respectively, by SN2 and modified Mitsunobu reactions. During the course of all
reactions, stereochemistry of the chiral centers were under controlling according to
the known reaction mechanisms. The resultant chiral N-tosylated enyne derivatives
afforded the corresponding chiral fused cyclopenta[c]pyridinone derivatives (69,
73, 75 and 77) with acceptable chemical yields and excellent diastereoslectivity
depending upon the conformational effect on the complete remote stereochemical
control for the newly generated chiral centers. The chemoenzymatic applications
done with biocatalysis (lipases) and the Pauson-Khand reaction are involved in
&ldquo / Green Chemistry&rdquo / approach.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12611176/index.pdf |
| Date | 01 October 2009 |
| Creators | Gumrukcu, Yasemin |
| Contributors | Tanyeli, Cihangir |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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