57956-49-7Relevant academic research and scientific papers
Reaction of silyl ketene acetals with epoxides: A new method for the synthesis of γ-butanolides
Maslak, Veselin,Matovi?, Radomir,Sai?i?, Radomir N.
, p. 8957 - 8966 (2004)
Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords butanolides in moderate/good yields. With epihalohydrins the reaction is regioselective and occurs at the less substituted end of the epoxide; the γ-haloalkyl-γ-butanolides thus obtained can be further transformed into various products. Graphical Abstract
Synthesis of 3-pyrrolin-2-ones by rhodium-catalyzed transannulation of 1-sulfonyl-1,2,3-triazole with ketene silyl acetal
Ran, Rui-Qiao,He, Jun,Xiu, Shi-Dong,Wang, Kai-Bing,Li, Chuan-Ying
supporting information, p. 3704 - 3707 (2014/08/05)
α-Imino rhodium carbenoids generated from 1-sulfonyl 1,2,3-triazole were applied to the 3 + 2 cycloaddition with ketene silyl acetal, offering a novel and straightforward synthesis of biologically interesting compound 3-pyrrolin-2-one with broad substrate scope.
CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2- arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-Aminophenyl)-2- carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist
Baron, Bruce M.,Cregge, Robert J.,Farr, Robert A.,Friedrich, Dirk,Gross, Raymond S.,Harrison, Boyd L.,Janowick, David A.,Matthews, Donald,McCloskey, Timothy C.,Meikrantz, Scott,Nyce, Philip L.,Vaz, Roy,Metz, William A.
, p. 995 - 1018 (2007/10/03)
(E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid, 1, is a potent and selective antagonist of the glycine site of the N-methyl-D-aspartate (NMDA) receptor. Using 3D comparative molecular field analysis (CoMFA) to guide the synthetic effort, a series of aryl diacid analogues of 1 were synthesized to optimize in vivo potency, duration of action, and binding activity. It was found that the incorporation of a substituted aromatic with an electron withdrawing group or a heterocyclic group at the 2-position of the 3-propenyl moiety of 1 gave compounds with better affinity and potency in the murine stroke model. Ultimately this led to the discovery of 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, 19, as a new potent selective glycine-site NMDA receptor antagonist.
Surface-mediated solid phase reaction. Part 9. A convenient procedure for aldol reaction of ketene silyl acetals with aldehydes on the solid surface of alumina
Ranu, Brindaban C.,Saha, Manika,Bhar, Sanjay
, p. 3065 - 3077 (2007/10/03)
The aldol reaction of ketene silyl acetals with aldehydes proceeds efficiently on the solid surface of alumina impregnated with anhydrous zinc chloride under sonication providing aldol products in high yields and with good stereoselectivity.
Reaction of Silyl Enol Ethers with Arenediazonium Salts. Part 2. α-Amination of Esters
Sakakura, Toshiyasu,Hara, Masayasu,Tanaka, Masato
, p. 289 - 294 (2007/10/02)
Diazonium salts efficiently serve as electrophilic aminating reagents of esters.The reaction of arenediazonium tetrafluoroborates with ketene silyl ketals yielded α-azo or α-hydrazono esters in good to excellent yields under very mild conditions.Hydrogenation of those esters gave α-amino esters quantitatively.
Reaction of Ketene Silyl Acetals with Diazonium Salts: a Novel α-Amino Acid Ester Synthesis
Sakakura, Toshiyasu,Tanaka, Masato
, p. 1309 - 1310 (2007/10/02)
The reaction of ketene silyl acetals with arenediazonium tetrafluoroborate gave α-hydrazono and α-azo esters, which were easily hydrogenated to α-amino esters.
