15288-14-9Relevant academic research and scientific papers
Enantioselective hydrolyses with Yarrowia lipolytica: A versatile strain for esters, enol esters, epoxides, and lactones
Fantin, Giancarlo,Fogagnolo, Marco,Guerrini, Alessandra,Medici, Alessandro,Pedrini, Paola,Fontana, Silvia
, p. 2709 - 2713 (2007/10/03)
Racemic secondary esters 1-3, γ-lactones 8-9, and styrene oxide 7 are kinetically resolved via hydrolysis with Yarrowia lipolytica YL2 strain. The enantioselective hydrolysis of prochiral enol esters 4-6 to the corresponding homochiral carbonyl compounds 13-15 is also described. Subsequent reduction of the ketone 13 and of the aldehyde 15 can be avoided using lyophilised cells.
Radical Addition Reactions of 2-(Phenylseleno)propanedioates to Alkenes and Alkynes
Byers, Jeffrey H.,Lane, Gregory C.
, p. 3355 - 3360 (2007/10/02)
Sunlamp photolysis of methyl or ethyl 2-(phenylseleno)propanedioate with a variety of alkenes and alkynes in benzene yielded addition products in good to excellent yields.The proposed mechanism involves a radical chain process in which addition of a malonate ester radical is followed by phenylseleno transfer.Monosubstituted alkenes, 1,1- and 1,2-disubstituted alkenes, terminal alkynes, and internal alkynes were shown to undergo this reaction.Addition to diallyl ether led to substituted tetrahydrofurans, characteristic of process involving initial addition, followed by cyclization prior to phenylseleno transfer.Vinyl arenes, conjugated dienes, and unsaturated carbonyl compounds proved unreactive.
Anti-Markovnikov Addition of Nucleophiles to a Non-conjugated Olefin via Single Electron Transfer Photochemistry
Gassman, Paul G.,Bottorff, Kyle J.
, p. 5449 - 5452 (2007/10/02)
Nucleophilic solvent has been added regiospecifically in an anti-Markovnikov manner to a simple non-conjugated olefin, 1-methylcyclohexene, through single electron transfer induced photochemistry using the 1-cyanonaphthalene - biphenyl pair for achieving photooxidation.
Electrophilic Cleavage of Cyclopropanes. Acetolysis of Bicyclic and Tricyclic Cyclopropanes
Wiberg, Kenneth B.,Kass, Steven R.,Meijere, Armin de,Bishop, K. C.
, p. 1003 - 1007 (2007/10/02)
The acetolysis of a series of bicycloalkanes and propellanes has been studied.The effect of ring strain, caused by changing ring size or introducing a trans-ring fusion, on the rate and products of the reaction has been examined.No correlation was found between rates of acetolysis and strain energy relief, but with the exception of propellane, there is a rough correlation with ionization potentials.The degree of polarization of the C-C bonds in the presence of a proton correlates very well with reactivity and is a controlling factor for the acetolysis rates.The importance of the energies of unoccupied orbitals with the appropriate symmetry in controlling electron polarization is shown by the large difference in rate of reaction between - and propellanes.
