517907-55-0Relevant academic research and scientific papers
Stereoselective synthesis of optically active cyclopenta[c]pyrans and cyclopenta[c]furans by the intramolecular Pauson-Khand reaction
Sezer, Serdar,Sahin, Ertan,Tanyeli, Cihangir
, p. 476 - 485 (2010)
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.
Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines
Sezer, Serdar,Guemruekcue, Yasemin,Bakirci, Irem,Yagiz Uenver,Tanyeli, Cihangir
, p. 662 - 669 (2012/09/22)
The intramolecular Pauson-Khand and ring closing metathesis (RCM) reactions of nitrogen containing chiral enynes and dienes are described. The enyne and diene systems comprised of N-propargylated and N-allylated units are constructed on chiral homoallylic
Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols
Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
, p. 2679 - 2687 (2007/10/03)
A chemoenzymatic methodology has been developed using indium-mediated allylation of heterocyclic aldehydes under aqueous conditions followed by Pseudomonas cepacia lipase-catalyzed enantioselective acylation of racemic homoallylic and homopropargylic alcohols in organic media. It is observed that the lipase immobilized on ceramic particles (PS-C Amano II) catalyzes the resolution in a highly enantioselective manner in less time as compared to the native enzyme (PS Amano). The approach provides new functionalized chiral synthons useful in the synthesis of natural and pseudonatural products.
