15197-68-9Relevant academic research and scientific papers
Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
Murai, Masahito,Nishimura, Kengo,Takai, Kazuhiko
, p. 2769 - 2772 (2019/03/23)
The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty
An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols
Heath, Rachel S.,Birmingham, William R.,Thompson, Matthew P.,Taglieber, Andreas,Daviet, Laurent,Turner, Nicholas J.
, p. 276 - 281 (2019/01/04)
Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.
A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling
Weigel, William K.,Dennis, Taylor N.,Kang, Amrik S.,Perry, J. Jefferson P.,Martin, David B. C.
supporting information, p. 6234 - 6238 (2018/10/05)
A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.
Scope and mechanism in palladium-catalyzed isomerizations of highly substituted allylic, homoallylic, and alkenyl alcohols
Larionov, Evgeny,Lin, Luqing,Gune, Laure,Mazet, Clment
supporting information, p. 16882 - 16894 (2015/01/09)
Herein we report the palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system. The operationally simple reaction protocol is applicable to a broad range of substrates and displays a wide functional group tolerance, and the products are usually isolated in high chemical yield. Experimental and computational mechanistic investigations provide complementary and converging evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences. Interestingly, the catalyst does not dissociate from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isomerization of alkenyl alcohols when additional substituents are present on the alkyl chain.
Intrazeolite photooxygenation of chiral alkenes. Control of facial selectivity by confinement and cation-π interactions
Stratakis, Manolis,Raptis, Christos,Sofikiti, Nikoletta,Tsangarakis, Constantinos,Kosmas, Giannis,Zaravinos, Ioannis-Panagiotis,Kalaitzakis, Dimitris,Stavroulakis, Dimitris,Baskakis, Constantinos,Stathoulopoulou, Aggeliki
, p. 10623 - 10632 (2007/10/03)
Depending on the nature of the substituents on the stereogenic carbon atom, the ene reaction of singlet oxygen with several chiral alkenes by confinement within thionin-supported zeolite NaY, may exhibit significant changes on facial selectivity by comparison to their photooxygenation reaction in solution. It is proposed that, apart from the conformational consequences as a result of the alkene confinement within the zeolite cavities, a synergism between Na+-π interactions and singlet oxygen-Na+ interactions plays a significant role in the transition states of ene hydroperoxidation. Within NaY, the diastereoselectivity may significantly depend on the site selectivity, as probed through specific deuterium labelling of trisubstituted alkenes bearing a gem-dimethyl group. In certain cases, a remote stereogenic centre relative to the reacting double bond may induce enhanced diastereoselection and regioselectivity.
Synthesis of aryl-substituted aldehydes and ketones via palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols
Larock,Leung,Stolz-Dunn
, p. 6629 - 6632 (2007/10/02)
The palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols affords excellent yields of aryl-substituted aldehydes and ketones.
THIAZOLYLMETHYLENETRIPHENYLPHOSPHORANE AND ITS BENZO DERIVATIVE: STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES. TWO-CARBON HOMOLOGATION OF ALDEHYDES.
Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
, p. 2021 - 2032 (2007/10/02)
The title thiazolyl phosphorane is a stable yet quite reactive Wittig-type reagent which uppon reaction with various aldehydes affords vinylthiazoles, mainly or exclusively as E-isomers, in very good yields.Also the benzothiazolyl phosphorane derivative, unlike a literature report, prove to react with aldehydes.Vinylthyazoles subjected to formyl deblocking from thiazole nucleous afford two-carbon homologated satured aldehydes.As an example, one of these vinylthiazoles, viz. the β-phenyl derivative 8f, proves to add n-butyl lithium cuprate to give after the formyl deblocking 3-phenylheptanal.
