64187-51-5Relevant academic research and scientific papers
Direct and practical Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams via the Thorpe-Ingold effect
Panagiotou, Maria,Demos, Vasileios,Magriotis, Plato Α.
supporting information, (2020/09/09)
A highly efficient Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams possessing a 4-aryl substituent is described, employing a direct, uncatalyzed Mannich reaction between TMS imines and TMS ketene acetals. The process avoids cryogenic conditions, making it more amenable to process-scale use than related methods for β-lactam synthesis. A Gilman-Speeter diastereoselective version using a sulfinyl imine and leading to homochiral sulfinyl β-aminoester is also presented.
Access to nitriles from aldehydes mediated by an oxoammonium salt
Kelly, Christopher B.,Lambert, Kyle M.,Mercadante, Michael A.,Ovian, John M.,Bailey, William F.,Leadbeater, Nicholas E.
supporting information, p. 4241 - 4245 (2015/04/14)
A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.
Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates
Hong, Kai,Morken, James P.
supporting information, p. 9252 - 9254 (2013/07/26)
We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s
Three-component coupling sequence for the regiospecific synthesis of substituted pyridines
Chen, Ming Z.,Micalizio, Glenn C.
supporting information; experimental part, p. 1352 - 1356 (2012/03/11)
A de novo synthesis of substituted pyridines is described that proceeds through nucleophilic addition of a dithiane anion to an α,β- unsaturated carbonyl followed by metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (generated in situ by the low-temperature reaction of lithium hexamethyldisilazide with an aldehyde) and Ag(I)- or Hg(II)-mediated ring closure. The process is useful for the convergent assembly of di- through penta-substituted pyridines with complete regiochemical control.
Catalytic intermolecular hetero-dehydro-diels-alder cycloadditions: Regioand diasteroselective synthesis of 5,6-dihydropyridin-2-ones
Fernandez-Garcia, Jesus Manuel,Fernandez-Rodriguez, Manuel A.,Aguilar, Enrique
supporting information; experimental part, p. 5172 - 5175 (2011/12/04)
A novel catalyzed intermolecular heterodehydro-Diels-Alder reaction between push-pull 1,3-dien-5-ynes and aldimines or silylaldimines is reported. The sequence is promoted both by gold(I) or silver(I) catalysts and leads to the diastereo- and regioselective formation of 5,6- dihydropyridin-2-ones.
T-CELL INHIBITING COMPOUNDS AND THEIR USE FOR THE TREATMENT OF T-CELL-MEDIATED DISEASES
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Page/Page column 26-27, (2008/12/07)
The present invention relates to compounds of formula IA or IB. The present invention also concerned to a method of treating immunologic diseases or pathological conditions in association with T cell involving an immunologic component using T-cell inhibitors, optionally in combination with one or more other drugs selected from steroids, DMARDs, NSAIDs, immunosuppressive, and biological modifiers, pharmaceutical compositions comprising said compounds of formula IA or IB together with said other drugs, and the use of T-cell inhibitors for the manufacture of a pharmaceutical composition for the treatment of immunologic diseases or pathological conditions involving an immunologic component.
Asymmetric synthesis of propargylamides via 3,3′-disubstituted binaphthol-modified alkynylboronates
Wu, T. Robert,Chong, J. Michael
, p. 15 - 18 (2007/10/03)
(Chemical Equation Presented) Alkynylboronates derived from 3,3′-disubstituted-2,2′-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective s
A one-pot aza-Wittig based solution and polymer supported route to amines
Hemming,Bevan,Loukou,Patel,Renaudeau
, p. 1565 - 1568 (2007/10/03)
This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.
A trans-stereoselective synthesis of 3-halo-4-alkyl(aryl)-NH-azetidin-2-ones
Bandini, Elisa,Favi, Gianfranco,Martelli, Giorgio,Panunzio, Mauro,Piersanti, Giovanni
, p. 1077 - 1079 (2007/10/03)
Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting β-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidino
Lithium perchlorate mediated three component reaction for the preparation of primary amines
Saidi, Mohammad R.,Javanshir, Shahrzad,Mojtahedi, Mohammad M.
, p. 330 - 331 (2007/10/03)
In the presence of lithium perchlorate in diethyl ether, LPDE, a three- component reaction between aldehydes, sodium hexamethyldisilazane or lithium hexamethyldisilazane, LHMDS, and different nucleophiles proceeds smoothly to afford primary amines in good yields.
