6922-90-3Relevant academic research and scientific papers
I-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions
Colas, Kilian,Dos Santos, A. Catarina V. D.,Mendoza, Abraham
supporting information, (2019/10/08)
The direct preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.
Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones
Liao, Yuan-Xi,Xing, Chun-Hui,Hu, Qiao-Sheng
supporting information; experimental part, p. 1544 - 1547 (2012/06/05)
Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.
Triphenylbutanamines: Kinesin spindle protein inhibitors with in vivo antitumor activity
Wang, Fang,Good, James A. D.,Rath, Oliver,Kaan, Hung Yi Kristal,Sutcliffe, Oliver B.,MacKay, Simon P.,Kozielski, Frank
supporting information; experimental part, p. 1511 - 1525 (2012/04/10)
The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-l-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit Kiapp ≥ 10 nM and GI50 ≈ 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.
Cinchona alkaloid phase-transfer catalysts revisited: Influence of substituted aryl groups on the enantioselectivity of glycine ester enolate alkylation
Kumar, Sanjeev,Ramachandran, Uma
, p. 7022 - 7028 (2007/10/03)
We report herein, the influence of substituted aryl groups in quaternary ammonium salts derived from cinchona alkaloids on enantioselectivity of the alkylation of glycine ester enolates.
Directed Metalation of Benzenesulfinamides. A Novel Route to Meta-Substituted Aromatic Compounds
Katritzky, Alan R.,Lue, Ping
, p. 74 - 78 (2007/10/02)
Directed lithiation ortho to the sulfinamide group of readily available ortho- and para-substituted N-phenylbenzenesulfinamides (5a-d) and reaction with a variety of electrophiles followed by mercuridesulfination (HgCl2) or dehydrodesulfination (Ra/Ni) co
ONE-STEP SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS IN THE PRESENCE OF A NICKEL(II)-PHOSPHINE CATALYST.
Fiandanese, V.,Marchese, G.,Ronzini, L.
, p. 3677 - 3680 (2007/10/02)
A one-step synthesis of diaryl and alkyl-aryl ketones by the reaction of carboxylic acid with Grignard reagents in the presence of NiCl2(Ph2PCH2CH2PPh2) as catalyst is described.In the nickel-catalyzed Grignard reaction the formation of alcohols is nearly completely suppressed.
