205641-94-7Relevant academic research and scientific papers
Pd-catalyzed synthesis of aryl and heteroaryl triflones from reactions of sodium triflinate with aryl (heteroaryl) triflates
Smyth, Lynette A.,Phillips, Eric M.,Chan, Vincent S.,Napolitano, José G.,Henry, Rodger,Shekhar, Shashank
, p. 1285 - 1294 (2016/02/19)
A novel method for Pd-catalyzed triflination of aryl and heteroaryl triflates using NaSO2CF3 as the nucleophile is described. The combination of Pd2(dba)3 and RockPhos formed the most effective catalyst. A broad range of functional groups and heteroaromatic compounds were tolerated under the neutral reaction conditions. The order of reactivity ArOTf ≥ ArCl ≥ ArBr is consistent with transmetalation being a slow step of the reaction.
Overturning indolyne regioselectivities and synthesis of indolactam V
Bronner, Sarah M.,Goetz, Adam E.,Garg, Neil K.
supporting information; experimental part, p. 3832 - 3835 (2011/04/27)
We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.
Indolyne experimental and computational studies: Synthetic applications and origins of selectivities of nucleophilic additions
Im, G-Yoon J.,Bronner, Sarah M.,Goetz, Adam E.,Paton, Robert S.,Cheong, Paul H.-Y.,Houk,Garg, Neil K.
supporting information; experimental part, p. 17933 - 17944 (2011/02/26)
Efficient syntheses of 4,5-, 5,6-, and 6,7-indolyne precursors beginning from commercially available hydroxyindole derivatives are reported. The synthetic routes are versatile and allow access to indolyne precursors that remain unsubstituted on the pyrrole ring. Indolynes can be generated under mild fluoride-mediated conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model has led to the design of a substituted 4,5-indolyne that exhibits enhanced nucleophilic regioselectivity.
BCL-2-SELECTIVE APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE DISEASES
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Page/Page column 259, (2010/06/20)
Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-2 or Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which are expressed anti-apoptotic Bcl-2 protein.
Synthesis of conformationally restrained, β-substituted derivatives of l-tryptophan via lewis acid-catalyzed reaction of 2,3-aziridino-β-d-lyxo-furanosides with 1-(trialkylsilyl)indoles
Hofmann, Bernhard,Dauban, Philippe,Biron, Jean-Philippe,Potier, Pierre,Dodd, Robert H.
, p. 473 - 487 (2007/10/03)
Reaction of 1-(triisopropylsilyl)indole (or its 5-benzyloxy derivative) with tert-butyldimethylsilyl N-(tert-butyloxycarbonyl)-2,3-aziridino-2,3-dideoxy5-O-methyl- (or benzyl-)-β-D-lyxofuranoside in the presence of boron trifluoride etherate gave, regio- and stereospecifically, the corresponding protected 2-amino-3-(3-indolyl)arabinofuranoside derivatives. These could be transformed, after desilylation, oxidation and removal of the Boc group, into 2-amino-3-(3-indolyl)arabinonolactone derivatives. The latter represent novel examples of conformationally restrained analogues of L-tryptophan as well as precursors of optically pure β-substituted L-tryptophans.
