1268368-69-9Relevant academic research and scientific papers
The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols
Ghebreghiorgis, Thomas,Biannic, Berenger,Aponick, Aaron,Kirk, Brian H.,Ess, Daniel H.
, p. 16307 - 16318,12 (2020/09/09)
Density functional calculations and experiment were used to examine the mechanism, reactivity, and origin of chirality transfer in monophosphine Au-catalyzed monoallylic diol cyclization reactions. The lowest energy pathway for cyclization involves a two-
Chirality transfer in Au-catalyzed cyclization reactions of monoallylic diols: Selective access to specific enantiomers based on olefin geometry
Aponick, Aaron,Biannic, Berenger
, p. 1330 - 1333 (2011/05/15)
The gold(I)-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is shown to be highly stereoselective when chiral allylic alcohols are employed. Substrates that differ only in olefin geometry provide enantiomeric products from formal SN2′ reactions in high yields with excellent chirality transfer. The allylic alcohol stereochemistry also efficiently controls the facial selectivity when the substrates include additional stereocenters.
A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
Biannic, Berenger,Ghebreghiorgis, Thomas,Aponick, Aaron
scheme or table, p. 802 - 807 (2011/07/30)
The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl) di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure MPA is an efficient scavenging reagent that halts the reaction progress.
