13735-78-9Relevant articles and documents
The β-Silyl Effect on the Memory of Chirality in Friedel-Crafts Alkylation Using Chiral α-Aryl Alcohols
Nokami, Toshiki,Yamane, Yu,Oshitani, Shunsuke,Kobayashi, Jun-Ka,Matsui, Shin-Ichiro,Nishihara, Takashi,Uno, Hidemitsu,Hayase, Shuichi,Itoh, Toshiyuki
, p. 3182 - 3185 (2015)
Iron salt-catalyzed Friedel-Crafts alkylation of chiral α-aryl alcohols with a trimethylsilyl group was found to proceed with retention of the configuration of the hydroxyl group as a leaving group. The memory of chirality of this system stems from the β-
Mild and efficient catalytic method for α-trimethylsilyl ketones
Sun, Chunrui,Li, Jingwei,Demerzhan, Silviya,Lee, Daesung
experimental part, p. 17 - 25 (2011/06/25)
A mild, efficient and convenient method for the synthesis of α-silyl ketones from corresponding aldehydes and trimethylsilyldiazomethane in the presence of a catalytic amount of indium(III) chloride has been developed. ARKAT-USA, Inc.
1,2- versus 1,3-Silyl migration in the reaction of acylsilanes with silyl-substituted carbanions
Puschke, Thomas,Lange, Jens,Schaumann, Ernst
, p. 2628 - 2630 (2008/09/19)
The Peterson olefination of acylsilanes 1 by silylated carbanions 5,14 to give alkenes 13,17 via a 1,3-silyl shift is favored by the stabilization of the carbanion intermediate 16 through two sulfide units versus one as in 12, while a combination of DMPS on 1 and TBS on 14 leads to 1,2-migration product 15.
Discovery of ((4R,5S)-5-amino-4-(2,4,5-trifluorophenyl)cyclohex-1-enyl)-3- (trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H-yl)methanone (ABT-341), a highly potent, selective, orally efficacious, and safe dipeptidyl peptidase IV inhibitor
Pei, Zhonghua,Li, Xiaofeng,Von Geldern, Thomas W.,Madar, David J.,Longenecker, Kenton,Yong, Hong,Lubben, Thomas H.,Stewart, Kent D.,Zinker, Bradley A.,Backes, Bradley J.,Judd, Andrew S.,Mulhern, Mathew,Ballaron, Stephen J.,Stashko, Michael A.,Mika, Amanda K.,Beno, David W. A.,Reinhart, Glenn A.,Fryer, Ryan M.,Preusser, Lee C.,Kempf-Grote, Anita J.,Sham, Hing L.,Trevillyan, James M.
, p. 6439 - 6442 (2008/01/27)
Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341),
Reaction of silylketenes with carbanions: Simple preparation of α- silylketones using organocerium reagents
Akai, Shuji,Kitagaki, Shinji,Matsuda, Satoshi,Tsuzuki, Yasunori,Naka, Tadaatsu,Kita, Yasuyuki
, p. 1135 - 1139 (2007/10/03)
Preparation of α-silylketones 1 by the reaction of three kinds of silylketenes 3a-c with various organometallic reagents 4 was studied. Although the use of n-BuLi, MeMgBr, Me2CuLi, Et3Al, and Et2Zn resulted in complicated reactions, organocerium reagents 4 (M=CeCl2) added selectively to the carbonyl carbon of 3 to generate enolate anions A, which were treated with aqueous NH4Cl or alkyl halides 5 to give 1. Seventeen α-silylketones 1a-q were prepared in 3199% yields from three components, 3, alkyl- or arylcerium reagents 4, and proton or alkyl halides 5. This method was applied to a regiocontrolled preparation of two isomeric α-silylketones 1r, s.
Reaction of acylsilanes with sulfur ylides. Selective formation of silyl enol ethers or β-ketosilanes
Nakajima, Tadashi,Segi, Masahito,Sugimoto, Fumitosi,Hioki, Reiko,Yokota, Seiko,Miyashita, Kiyoshi
, p. 8343 - 8358 (2007/10/02)
The reaction of acylsilanes with sulfur ylides in THF results in the formation of the corresponding silyl enol ethers or β-ketosilanes. The relative ratio of these products varies with the ylide conditions and the stability of ylide used. It is noteworthy that silyl enol ethers were formed under the salt-free ylide conditions, and that β-ketosilanes were yielded in the presence of soluble inorganic salts in THF, selectively. The formation of both products would be interpreted in terms of the anionotropic and cationotropic rearrangements of silyl group in the reaction intermediate.
Silicon-Directed Diene Synthesis
Brown, Paul A.,Bonnert, Roger V.,Jenkins, Paul R.,Lawrence, Nicholas J.,Selim, Mohammed R.
, p. 1893 - 1900 (2007/10/02)
A synthesis of 2-substituted-1,3-dienes is reported which uses silicon as a control element: eight aldehydes were converted into α-silyl ketones by treatment with trimethylsilylmethylmagnesium chloride and rapid Collins oxidation.Addition of vinylmagnesiu
Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes
Fuerstner, Alois,Kollegger, Gerlinde,Weidmann, Hans
, p. 295 - 305 (2007/10/02)
Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively.Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson olefination sequence.These reactions allow the selective formation of vinylsilanes.
Syntheses of Vinyl Silane Phosphates: Novel Synthetic Intermediates
Koerwitz, Frederick L.,Hammond, Gerald B.,Wiemer, David F.
, p. 738 - 743 (2007/10/02)
A number of procedures have been developed for the synhesis of vinyl silane phosphates (VSP's), a new type of functional group bearing trialkylsilyl and diaryl (or dialkyl) phosphate groups on adjacent sp2 carbons. α-Silyl ketone enolates, acce
A SILICON DIRECTED DIENE SYNTHESIS
Brown, Paul A.,Bonnert, Roger V.,Jenkins, Paul R.,Selim, Mohammed R.
, p. 693 - 696 (2007/10/02)
A convenient method for the conversion of a series of aldehydes into substituted dienes is reported which uses silicon as a control element.
