74426-28-1Relevant academic research and scientific papers
Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions
Kooti,Kooshki,Nasiri
, p. 2641 - 2656 (2019/02/14)
A new catalyst has been prepared via immobilization of Cu(proline)2 complex onto the surface of magnetic graphene. The fabricated nanocatalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD) analysis, vibrating-sample magnetometry (VSM), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), inductively coupled plasma (ICP) techniques, and elemental analysis. Its catalytic performance was investigated in the aldol reaction using a mild and ecofriendly procedure. The synthesized nanocomposite, which contains Cu(II) center as Lewis acid, was found to be an efficient catalyst for asymmetric aldol reactions, affording corresponding aldol products in high yield and excellent enantiomeric excess (> 90?%). The examined catalyst was prepared from low-cost, easily available starting materials and can be readily isolated by magnetic decantation for recycling and reuse in consecutive reactions without significant loss of activity.
Visible-light-mediated achmatowicz rearrangement
Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
supporting information, p. 30 - 33 (2017/11/28)
Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.
Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols
Qi, Shan-Bin,Li, Min,Li, Shijun,Zhou, Ji-Ning,Wu, Jun-Wen,Yu, Feng,Zhang, Xi-Chang,Chan, Albert S.C.,Wu, Jing
, p. 929 - 937 (2013/02/26)
The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the
Room temperature and highly enantioselective additions of alkyltitanium reagents to aldehydes catalyzed by a titanium catalyst of (R)-h 8-binol
Li, Qinghan,Gau, Han-Mou
experimental part, p. 929 - 939 (2012/06/29)
Three alkyltitanium reagents of RTi(O-i-Pr)3 (R = Cy (1a), i-Bu (1b), and n-Bu (1c)) were prepared in good yields. The high-resolution mass spectroscopy showed that 1b and 1c in the gas phase are monomeric species. However, the solid state of 1a revealed a dimeric structure. Asymmetric additions of 1a-1c to aldehydes catalyzed by a titanium catalyst of (R)-H 8-BINOL were studied at room temperature. The reactions produced desired secondary alcohols in good yields with good to excellent enantioselectivities of up to 94% ee. Reactivity and enantioselectivity differences, in terms of steric bulkiness of the R nucleophiles, are herein described. The addition reactions of secondary c-hexyl to aldehydes were slower than the reactions of primary i-butyl or n-butyl nucleophiles. For the primary alkyls, lower enantioselectivities were obtained for products from addition reactions of the linear n-butyl as compared with the enantioselectivities of products from the addition reactions of the branched i-butyl group. The same stereochemistry of RTi(O-i-Pr)3 addition reactions as the addition reactions of organozinc, organoaluminum, Grignard, or organolithium reagents directly supports the argument of that titanium-catalyzed addition reactions of aldehydes involve an addition of an organotitanium nucleophile.
Catalytic enantioselective synthesis of sterically demanding alcohols using di(2°-alkyl)zinc prepared by the refined Charette's method
Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki
supporting information; experimental part, p. 5443 - 5445 (2010/10/04)
A highly practical, catalytic enantioselective 2°-alkyl addition to aldehydes and ketones was developed. Chiral phosphoramide ligand (1) with salt-free and solvent-free di(2°-alkyl)zinc reagents prepared from (2°-alkyl)MgCl was essential. The Royal Society of Chemistry 2010.
Synthesis of Optically Active 2-Furylmethanols as Useful Chiral Building Blocks and Its Application to the Synthesis of (5R,6S)-6-Acetoxyhexadecan-5-olide and (+)-Disparlure
Kametani, Tetsuji,Tsubuki, Masayoshi,Tatsuzaki, Yoko,Honda, Toshio
, p. 639 - 646 (2007/10/02)
Kinetic resolution of racemic secondary 2-furylmethanols using catalytic amounts of the titanium(IV)-tartrate complex was achieved successfully, providing optically active 2-furylmethanols (80 - >98percent ee) and corresponding pyranones. (S)-1-(2-Furyl)undecanol (1f) was utilised as a chiral building block in the synthesis of (5R,6S)-6-acetoxyhexadecan-5-olide and (+)-disparlure.
Kinetic resolution of 2-furylcarbinols using the Sharpless oxidation and its application to the synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide
Kametani, Tetsuji,Tsubuki, Masayoshi,Tatsuzaki, Yoko,Honda, Toshio
, p. 2107 - 2110 (2007/10/02)
Kinetic resolution of 2-furylcarbinols employing 10 mol% of Ti(OiPr)4 in the presence of molecular sieves 3A under the Sharpless oxidation condition generally affords corresponding optically active 2-furylcarbinols in a range of 80-9
