517907-46-9Relevant academic research and scientific papers
Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
Mori-Quiroz, Luis M.,Maloba, Emmanuel W.,Maleczka, Robert E.
supporting information, p. 5724 - 5728 (2021/07/31)
4-Silyl-5,6-dihydropyrans undergo remarkably selective [1,4]-Wittig rearrangements to give silylcyclopropanes in good yields. The selectivity is independent of the silyl group, but it is influenced by the electronic character of the migrating center. Elec
Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
Sherwood, Alexander M.,Williamson, Samuel E.,Johnson, Stephanie N.,Yilmaz, Anil,Day, Victor W.,Prisinzano, Thomas E.
, p. 980 - 992 (2018/01/27)
A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated
Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines
Sezer, Serdar,Guemruekcue, Yasemin,Bakirci, Irem,Yagiz Uenver,Tanyeli, Cihangir
scheme or table, 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
Stereoselective synthesis of optically active cyclopenta[c]pyrans and cyclopenta[c]furans by the intramolecular Pauson-Khand reaction
Sezer, Serdar,Sahin, Ertan,Tanyeli, Cihangir
scheme or table, p. 476 - 485 (2010/07/04)
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.
A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization
Kim, Ikyon,Kim, Sun Gi,Kim, Ji Young,Lee, Ge Hyeong
, p. 8976 - 8981 (2008/03/18)
We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another
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.
