140846-38-4Relevant academic research and scientific papers
Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols
Musolino, Stefania F.,Ojo, O. Stephen,Westwood, Nicholas J.,Taylor, James E.,Smith, Andrew D.
supporting information, p. 18916 - 18922 (2016/12/26)
The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.
Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with allylB(pin)
Le, Hai,Batten, Amanda,Morken, James P.
supporting information, p. 2096 - 2099 (2014/05/06)
Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation ca
Synthesis and properties of BF2-3,3′- dimethyldiarylazadipyrromethene near-infrared fluorophores
Wu, Dan,O'Shea, Donal F.
supporting information, p. 3392 - 3395 (2013/07/26)
The first synthesis of both organic and aqueous soluble BF2 chelated 3,3′-dimethyl-5,5′-diarylazadipyrromethenes has been achieved. The fluorophores are emissive in organic and aqueous solvents with high quantum yields in the key biological near-infrared (NIR) spectral region of 675-700 nm. Following efficient cellular uptake from aqueous media the fluorophore can be readily visualized with confocal microscopy.
Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide
Provencher, Brian A.,Bartelson, Keith J.,Liu, Yan,Foxman, Bruce M.,Deng, Li
supporting information; experimental part, p. 10565 - 10569 (2011/12/05)
Unprecedented phase-transfer catalysts for the first example of an organocatalytic asymmetric conjugate addition of cyanide with acetone cyanohydrin are reported (see scheme). Utilizing an accessible cupreidinium salt and a cyanation reagent suitable for industrial scale, this reaction holds significant promise for practical asymmetric synthesis. The catalysts were developed as a result of key structural insights gained by X-ray analysis. Copyright
One-pot synthesis of optically active allyl esters via lipase-vanadium combo catalysis
Akai, Shuji,Hanada, Ryosuke,Fujiwara, Noboru,Kita, Yasuyuki,Egi, Masahiro
supporting information; experimental part, p. 4900 - 4903 (2011/01/12)
The combination of vanadium-oxo compounds (3 or 4) with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.
Electrochemical regeneration of chromium(II). Alkenylation of carbonyl compounds
Kuroboshi, Manabu,Tanaka, Muneaki,Kishimoto, Suguru,Tanaka, Hideo,Torii, Sigeru
, p. 69 - 70 (2007/10/03)
Electrochemical alkenylation of aldehydes using an Al sacrificial anode in the presence of Cr(II)/Ni(II) catalysts afforded the corresponding allyl alcohol derivatives in good to moderate yields.
Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes
Kuroboshi, Manabu,Tanaka, Muneaki,Kishimoto, Suguru,Goto, Kentaro,Tanaka, Hideo,Torii, Sigeru
, p. 2785 - 2788 (2007/10/03)
Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.
