10519-20-7Relevant articles and documents
cis-Semihydrogenation of alkynes with amine borane complexes catalyzed by gold nanoparticles under mild conditions
Vasilikogiannaki, Eleni,Titilas, Ioannis,Vassilikogiannakis, Georgios,Stratakis, Manolis
supporting information, p. 2384 - 2387 (2015/02/05)
Supported gold nanoparticles catalyze the semihydrogenation of alkynes to alkenes with ammonia borane or amine borane complexes in excellent yields and under mild conditions. Internal alkynes provide cis-alkenes, making this protocol an attractive alternative of the classical Lindlar's hydrogenation.
Topological study of mechanistic diversity in conjugated fatty acid biosynthesis
Bhar, Palash,Reed, Darwin W.,Covello, Patrick S.,Buist, Peter H.
supporting information; scheme or table, p. 6686 - 6690 (2012/08/27)
Variations on an oxidative theme: The precision with which FAD2-type desaturases carry out C-H activation reactions on flexible lipidic substrates is astonishing. The conformational space available within the active site of these enzymes has been explored using deuterium-labeled substrates, and evidence for a novel quasi-eclipsed conformer has been uncovered. The scheme shows some prototypical substrate conformations. Copyright
Deuteration of α,β-acetylenic esters, amides, or carboxylic acids without using deuterium gas: Synthesis of 2,2,3,3-tetradeuterioesters, amides, or acids
Concellón, José M.,Rodríguez-Solla, Humberto,Concellón, Carmen
, p. 2129 - 2131 (2007/10/03)
An easy, simple, rapid, and nonhazardous deuteration of the C-C triple bond of α,β-acetylenic esters, amides, or acids by means of samarium diiodide in the presence of D2O, provides an efficient method for synthesizing 2,2,3,3-tetradeuterioesters, amides, or carboxylic acids, respectively. When H2O is used instead of D2O, saturated carboxylic esters, amides, or acids were isolated. A mechanism to explain these reduction reactions has been proposed.
Synthesis of Linoleic Acid with Chiral Isotopic Labelling at a Flanking and a Medial Allylic Methylene: the (8R,9Z,12Z)- and (11R,9Z,12Z)--Stereoisomers, and (Z)-Non-3-enal
Crombie, Leslie,Heavers, Andrew D.
, p. 1929 - 1938 (2007/10/02)
-Oct-2-ynal is converted by fermenting bakers' yeast into (1S)-oct-2-yn-1-ol with an enantiomeric purity of >96percent as measured by Mosher's MTPA method.The alcohol, as its tosyl ester, was then converted by copper-catalysed coupling with the di-Grignard of dec-9-ynoic acid and catalytic semi-hydrogenation, into (11R)-linoleic acid having less than 2percent E-material and >95 atom percentD.Provision for (11S)-linoleic acid was made by configurational inversion of (1R)-oct-2-yn-1-ol using Mitsunobu chemistry.(8R)-Linoleic acid is made by a similar approach, the labelled chiral centre being formed on (8S)-8-hydroxy-octanoic acid (>96percent ee).Reaction of the corresponding tosate with lithium acetylide-ethylenediamine complex gave, with configurational inversion, (8R)-dec-9-ynoic acid, built into (8R)-linoleic acid.A degradative circuit is applied to estimate the extent of configurational inversion in the displacement.Mitsunobu inversion of the (8S)-8-hydroxy compound provides access to (8S)-linoleic acid. (Z)-Non-3-enal, a labile aldehyde from the enzymic degradation of linoleic acid, is made in -labelled form by a synthesis which uses, as a key step, the reaction between triheptynylborane and deuteriodiazoacetic ester.
(Ethoxycarbonyliodomethyl)triphenylphosphonium Iodide: A Convenient Reagent for the Direct Synthesis of β-Substituted Propiolic Acids via the Corresponding Esters
Chenault, Jaques,Dupin, Jean-Francois E.
, p. 498 - 499 (2007/10/02)
Reaction between (ethoxycarbonyliodomethyl)triphenylphosphonium iodide, potassium carbonate, and various aromatic or aliphatic aldehydes in a liquid solid two phases system gives β-substituted propiolic esters.The corresponding acids are obtained in good yield by hydrolysis.
