98758-79-3Relevant academic research and scientific papers
Preparation of aliphatic ketones through a ruthenium-catalyzed tandem cross-metathesis/allylic alcohol isomerization
Finnegan, David,Seigal, Benjamin A.,Snapper, Marc L.
, p. 2603 - 2606 (2007/10/03)
Grubbs' 2nd generation and Hoveyda-Grubbs' ruthenium alkylidenes are shown to be effective catalysts for cross-metatheses of allylic alcohols with cyclic and acyclic olefins, as well as isomerization of the resulting allylic alcohols to alkyl ketones. The net result of this new tandem methodology is a single-flask process that provides highly functionalized, ketone-containing products from simple allylic alcohol precursors.
Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols
Amador, Marta,Ariza, Xavier,Garcia, Jordi,Sevilla, Sara
, p. 4511 - 4514 (2007/10/03)
(Matrix Presented) A new stereodivergent route to erythro- and threo-β-substituted serines from a common C2-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereo
The Stereochemistry of the 1,4-Elimination of Thiocyanic Acid from Hex-3-ene-2,5-diyl Dithiocyanates
Schoepfer, Joseph,Eichenberger, Eugen,Neier, Reinhard
, p. 246 - 248 (2007/10/02)
The elimination of thiocyanic acid from the stereoisomers of the hex-3-ene-2,5-diyl dithiocyanates, 4a, 4b, 6a and 6b, in the presence of a strong neutral base in an organic solvent, yields mixtures of the hex-2,4-dien-2-yl thiocyanates 9, 10 and 11 via a preferentially syn process.
ASSESSMENT OF BUTENE-1,4-DIOLS AS STARTING MATERIALS FOR THE PREPARATION OF ?-ALLYLTRICARBONYLIRON COMPLEXES
Bates, Roderick W.,Diez-Martin, David,Kerr, William J.,Knight, Julian G.,Ley, Steven V.,Sakellaridis, Anna
, p. 4063 - 4082 (2007/10/02)
This work assesses the use of butene-1,4-diols as starting materials for the synthesis of ?-allyltricarbonyliron lactone complexes.It has been shown that substituents, and the use of Lewis acids, mainly ZnBr2, in reactions with Fe2(CO)9 in benzene under ultrasonic conditions or in THF, greatly influence the yield and the product distribution.
Stereo-and Regioselective Palladium-Catalyzed 1,4-Diacetoxylation of 1,3-Dienes
Baeckvall, Jan-E.,Bystroem, Styrbjoern E.,Nordberg, Ruth E.
, p. 4619 - 4631 (2007/10/02)
Palladium-catalyzed oxidation of 1,3-dienes in acetic acid using an oxidation system of MnO2 and catalytic amounts of p-benzoquinone selectively gives 1,4-diacetoxy-2-alkenes.The reaction proceeds with high stereo-and regioselectivity, and by ligand control the reaction can be made to take place with either cis or trans 1,4-diacetoxylation across the diene in cyclic systems.Also in an acyclic system the 1,4-relative stereochemistry can be controlled as shown by the stereoselective oxidation of (E,E)- and (E,Z)-2,4-hexadiene to their corresponding dl (>88percent dl) and meso (>95percent meso) diacetates 15 and 18, respectively.Evidence is provided that supports a mechanism involving a trans acetoxypalladation of the conjugated diene to give an intermediate (?-allyl)palladium complex, followed by either a cis or trans attack by acetate on the allyl group.The cis attack is best explained by a cis migration from a (?-allyl)palladium intermediate.The diacetoxylation reaction was applied to the preparation of a key intermediate for the synthesis of dl-shikimic acid.
