779342-75-5Relevant academic research and scientific papers
γ-Selective Vinylogous Aza-Morita-Baylis-Hillman Reaction with N -Carbamoylimines
Gondo, Naruhiro,Tanigaki, Yusuke,Ueda, Yoshihiro,Kawabata, Takeo
supporting information, p. 398 - 402 (2020/02/27)
Vinylogous aza-Morita-Baylis-Hillman (aza-MBH) reactions of a vinylcyclopentenone with N -Boc imines provide the corresponding γ-adducts in high regioselectivity (10 examples). While the corresponding reactions with N -Ts imines give the α-adducts and γ-a
Enantioselective Construction of Sulfur-Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α-Sulfanyl Cyclic Ketones
Ye, Xueqian,Pan, Yongkai,Chen, Yunrong,Yang, Xiaoyu
, p. 3374 - 3379 (2020/07/16)
Asymmetric functionalizations of α-sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur-containing tetrasubstituted stereocenters were accessed via these methods, with excellent regioselectivities and high stereoselectivities. (Figure presented.).
Silver-Catalyzed Enantioselective Mannich Reaction of Diazoacetate Esters with N-Boc Aldimines
Robertson, Gerard P.,Farley, Alistair J. M.,Dixon, Darren J.
, p. 2785 - 2792 (2020/02/04)
The highly enantioselective Mannich reaction of diazoacetate esters with N-Boc aldimines catalyzed by silver(I) triflate in the presence of (R)-DM-SEGPHOS is reported. The reaction is broad in scope with respect to the (hetero)aromatic aldehyde-derived al
Direct enantioselective Mannich reactions of α-azido cyclic ketones: Asymmetric construction of chiral azides possessing an α-quaternary stereocenter
Ye, Xueqian,Pan, Yongkai,Yang, Xiaoyu
, p. 98 - 101 (2019/12/25)
Direct enantioselective Mannich reactions of α-azido cyclic ketones with aldimines are realized through chiral phosphoric acid catalysis, which generate chiral azides possessing an α-quanternary stereocenter with complete regioselectivities and high diast
Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
Kardile, Rahul Dadabhau,Liu, Rai-Shung
, p. 6452 - 6456 (2019/09/06)
Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives
Sun, Bo,Pluta, Roman,Kumagai, Naoya,Shibasaki, Masakatsu
, p. 526 - 529 (2018/02/10)
A direct catalytic Mannich-type reaction of α-oxygen-functionalized amides was achieved. The use of 7-azaindoline amide was crucial to facilitate direct enolization and subsequent stereoselective addition to imines in a cooperative catalytic system comprising a soft Lewis acid and Br?nsted base. The operationally simple room-temperature protocol furnished a syn-Mannich adduct with high stereoselectivity. Divergent functional group transformation of the amide moiety of the product allowed for expeditious access to enantioenriched syn-configured α-hydroxy-β-amino carboxylic acid derivatives, highlighting the synthetic utility of the present catalysis.
ISOINDOLINONE INHIBITORS OF THE MDM2-P53 INTERACTION AND PROCESS FOR MAKING THEM
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, (2018/10/25)
The invention relates to processes for preparing isoindolin-1-one derivatives, and in particular processes for preparing (2S,3S)-3-(4-chlorophenyl)-3-[(1R)-1-(4-chlorophenyl)-7-fluoro-5-[(1S)-1-hydroxy-1- (oxan-4-yl)propyl]-1-methoxy-3-oxo-2,3-dihydro-1H-
Enantioselective Additions of Stabilized Carbanions to Imines Generated from α-Amido Sulfones by Using Lipophilic Salts of Chiral Tris(1,2-diphenylethylenediamine) Cobalt(III) Trications as Hydrogen Bond Donor Catalysts
Joshi, Hemant,Ghosh, Subrata K.,Gladysz, John A.
, p. 3905 - 3915 (2017/08/29)
The enantiopure salt -[Co((S, S)-dpen) 3 ] 3+ 2Cl - BAr f - [BAr f = B(3,5-C 6 H 3 (CF 3) 2) 4 ] is an effective hydrogen bond donor catalyst (10 mol%, r.t., CH 2 Cl 2) for enantioselective additions of dialkyl malonates to Boc-derivatized aryl imines generated from sulfones [ArCH(SO 2 Ph)NHBoc] in the presence of K 2 CO 3 (ten examples, 91-97% isolated yields, 87-99% ee). The diastereomeric salt Λ-[Co((S, S)-dpen) 3 ] 3+ 2Cl - BAr f20 - [BAr f20 - = B(C 6 F 5) 4 - ] is similarly applied to additions of nitroalkanes (four examples, 89-93% isolated yields, 79-91% ee). Precautions to exclude air or moisture are unnecessary.
Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Br?nsted Acid-Base Catalyst with Recycle
Tsukanov, Sergey V.,Johnson, Martin D.,May, Scott A.,Rosemeyer, Morgan,Watkins, Michael A.,Kolis, Stanley P.,Yates, Matthew H.,Johnston, Jeffrey N.
, p. 215 - 226 (2016/03/04)
A stereoselective aza-Henry reaction between an arylnitromethane and Boc-protected aryl aldimine using a homogeneous Br?nsted acid-base catalyst was translated from batch format to an automated intermittent-flow process. This work demonstrates the advanta
Efficient synthesis of α-(N-Boc)aminoamides by addition of a carbamoylsilane to N-Boc-imines
Guo, Qilin,Wen, Xueping,Chen, Jianxin
, p. 8117 - 8122 (2016/11/19)
N,N-Dimethylcarbamoyl(trimethyl)silane reacted with N-Boc-imines in anhydrous benzene under catalysts-free conditions to afford N-Boc-protected α-amino amides in good yields (72-89%). The electronic property and the steric hindrance of substituent on the N-Boc-imines affected the reaction.
