166371-89-7Relevant academic research and scientific papers
Stereo- and Chemo-Selectivity in reduction of α-alkyl Aryl Ketones with Metal Hydrides
Aoki, Ikuo,Nishibayashi,Uemura, Sakae
, p. 337 - 340 (1995)
Metal hydride reduction of a variety of α-alkyl aryl ketones gives a mixture of threo- and erythro-β-aryl-β-hydroxyalkyl phenyl(or methyl)selenides by carbonyl reduction and 1-aryl-1-alkanol by the substitution of a phenyl(or methyl)seleno group with hydrogen.With all metal hydrides examined the formation of the threo-isomer always predominated.The addition of various metal chlorides in the reduction of various α-heteroatom (N, P, O, S)-substituted ketones.
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
supporting information, p. 380 - 384 (2020/10/30)
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
Homoleptic cobalt(II) phenoxyimine complexes for hydrosilylation of aldehydes and ketones without base activation of cobalt(II)
Hori, Momoko,Ishikawa, Ryuta,Koga, Yuji,Matsubara, Kouki,Mitsuyama, Tomoaki,Shin, Sayaka
, p. 1379 - 1387 (2021/05/29)
Air-stable, easy to prepare, homoleptic cobalt(II) complexes bearing pendant-modified phenoxyimine ligands were synthesized and determined. The complexes exhibited high catalytic performance for reducing aldehydes and ketones via catalytic hydrosilylation, where a hydrosilane and a catalytic amount of the cobalt(II) complex were added under base-free conditions. The reaction proceeded even in the presence of excess water, and excellent functional-group tolerance was observed. Subsequent hydrolysis gave the alcohol in high yields. Moreover, H2O had a critical role in activation of the Co(II) catalyst with hydrosilane. Several additional results also indicated that the cobalt(II) center acts as an active catalyst in the hydrosilylation of aldehydes and ketones.
COMPOUNDS, COMPOSITIONS, AND METHODS OF USE
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Paragraph 0259, (2020/12/11)
Described herein are compounds that act as CYP46A1 inhibitors, compositions comprising these compounds, and methods of their use into treating neurodegenerative diseases and the like, or a pharmaceutically active salt thereof. The present invention relates to compounds represented by the formula wherein each symbol is as defined in the specification, or a pharmaceutically active salt thereof.
Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier
Garg, Nidhi,Paira, Soumen,Sundararaju, Basker
, p. 3472 - 3476 (2020/05/29)
Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.
Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols
Kuciński, Krzysztof,Hreczycho, Grzegorz
, p. 552 - 555 (2020/02/04)
A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at room temperature under mild conditions.
Observation of hyperpositive non-linear effect in catalytic asymmetric organozinc additions to aldehydes
Geiger, Yannick,Achard, Thierry,Maisse-Fran?ois, Aline,Bellemin-Laponnaz, Stéphane
supporting information, p. 1250 - 1256 (2020/07/25)
Asymmetric amplification is a phenomenon that is believed to play a key role in the emergence of homochirality in life. In asymmetric catalysis, theoretical and experimental models have been investigated to provide an understanding of how chiral amplification is possible, in particular based on non-linear effects. Interestingly, it has been proposed a quarter century ago that chiral catalysts, when not enantiopure might even be more enantioselective than their enantiopure counterparts. We show here that such hyperpositive non-linear effect in asymmetric catalysis is indeed possible. An in-depth study into the underlying mechanism was carried out, and the scheme we derive differs from the previous proposed models.
Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation
Magre, Marc,Paffenholz, Eva,Maity, Bholanath,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 14286 - 14294 (2020/09/15)
A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones
Kuciński, Krzysztof,Hreczycho, Grzegorz
, p. 1912 - 1915 (2019/04/27)
Commercially available and inexpensive lithium triethylborohydride (LiHBEt3) acts as efficient catalyst for the solvent-free hydroboration of a wide range of aldehydes and ketones, which were subsequently transformed to corresponding 1° and 2° alcohols in one-pot procedure at room temperature (rt).
Supramolecular Interlocked Biphenyl Ligands for Enantioselective Ti-Catalyzed Alkylation of Aromatic Aldehydes
Scholtes, Jan Felix,Trapp, Oliver
supporting information, p. 3955 - 3960 (2019/07/03)
The substitution of tropos 2,2′-biphenols with (S)-amino-acid-derived interaction sites in the 5,5′-position results in a spontaneous desymmetrization. This process is driven by well-defined intermolecular hydrogen bonding, which leads to diastereoselecti
