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Stereoselective synthesis of optically active cyclopenta[c]pyrans and cyclopenta[c]furans by the intramolecular Pauson-Khand reaction
Date
2010-03-16
Author
Sezer, Serdar
ŞAHİN, Ertan
Tanyeli, Cihangir
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This work is licensed under a
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An intramolecular Pauson-Khand reaction of enynes derived from homoallyl, homopropargyl, and allyl alcohols is described. 2-Heteroaryl-substituted homoallyl, homopropargyl, and allyl alcohols are easily and efficiently resolved through enzymatic resolution in high ee (91-99%) and 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 the sole product, whereas enantiomerically enriched enynes derived from allyl alcohols give a diastereomeric cis:trans mixture of the cyclopenta[c]furan ring system.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Catalysis
URI
https://hdl.handle.net/11511/34908
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2010.02.016
Collections
Department of Chemistry, Article