2129-95-5Relevant articles and documents
Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes
Steinreiber, Andreas,Mayer, Sandra F.,Saf, Robert,Faber, Kurt
, p. 1519 - 1528 (2001)
Asymmetric biohydrolysis of trialkyl oxiranes (±)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols 1b-3b in up to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence was investigated by 18O-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity.
Superelectrophilic Fe(III)-Ion Pairs as Stronger Lewis Acid Catalysts for (E)-Selective Intermolecular Carbonyl-Olefin Metathesis
Albright, Haley,Schindler, Corinna S.,Vonesh, Hannah L.
supporting information, p. 3155 - 3160 (2020/04/21)
An intermolecular carbonyl-olefin metathesis reaction is described that relies on superelectrophilic Fe(III)-based ion pairs as stronger Lewis acid catalysts. This new catalytic system enables selective access to (E)-olefins as carbonyl-olefin metathesis products. Mechanistic investigations suggest the regioselective formation and stereospecific fragmentation of intermediate oxetanes to be the origin of this selectivity. The optimized conditions are general for a variety of aryl aldehydes and trisubstituted olefins and are demonstrated for 28 examples in up to 64% overall yield.
Alkylation of 2-substituted (6-Methyl-2-pyridyl)methyllithium species with epoxides
Vyvyan, James R.,Brown, Rebecca C.,Woods, Brian P.
supporting information; experimental part, p. 1374 - 1376 (2009/07/04)
Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted (6-methyl-2-pyridyl)methyllithium deriv
