In this thesis, an intramolecular Pauson-Khand reaction of chiral enynes
derived from homoallyl, allyl and homopropargyl alcohols is described. For this
purpose, 2-heteroaryl substituted homoallyl, allyl and homopropargyl alcohols are
easily and efficiently resolved through enzymatic resolution in a high ee (91-99%)
with a known stereochemistry. Each enantiomerically enriched enyne derived from
homoallyl and homopropargyl alcohols affords the conformationally most stable
diastereomeric cyclopenta[c]pyran ring system as a sole product, whereas
enantiomerically enriched enynes derived from allyl alcohols give the diastereomeric
cis:trans mixture of cyclopenta[c]furan ring system. In addition these, an
intramolecular Pauson&ndash / Khand reaction of camphor tethered enynes derived from
homoallyl, homomethallyl, and homopropargyl alcohols is also described.
Accordingly, homoallyl, homomethallyl, and homopropargyl moieties are easily
constructed on the camphor carbonyl group with excellent diastereoselectivity due to
endo-face selectivity, and with known stereochemistry. Each enantiomerically pure
enyne affords the conformationally most stable diastereomeric spirocyclic
cyclopenta[c]pyran ring system.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12613908/index.pdf |
| Date | 01 December 2011 |
| Creators | Sezer, Serdar |
| Contributors | Tanyeli, Cihangir |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | Ph.D. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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