93136-91-5Relevant articles and documents
Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation
Pismataro, Maria Chiara,Horenstein, Nicole A.,Stokes, Clare,Quadri, Marta,De Amici, Marco,Papke, Roger L.,Dallanoce, Clelia
, (2020/08/19)
The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity
A smooth rearrangement of N-p-toluenesulfonyl 2-tert- butyldiphenylsilylmethyl-substituted azetidines into N-p-toluenesulfonyl 3-tert-butyldiphenylsilyl-substituted pyrrolidines
Narhe, Bharat D.,Sriramurthy, Vardhineedi,Yadav, Veejendra K.
experimental part, p. 4390 - 4399 (2012/07/14)
The rearrangement of N-p-toluenesulfonyl 2-tert-butyldiphenylsilylmethyl- substituted azetidines into 3-tert-butyldiphenylsilyl-substituted pyrrolidines under Lewis acid conditions in dichloromethane involves 1,2-migration of silicon through a siliranium ion. The formation of siliranium ion was discovered not to be in concert with σC-N cleavage from stereochemical analysis of the pyrrolidine products formed from 3- and 4-substituted-2-tert- butyldiphenylsilylmethyl azetidines and also from the optical rotation data and chiral HPLC analysis of the pyrrolidine product formed from N-p-toluenesulfonyl 2(R)-tert-butyldiphenylsilylmethyl azetidine. The formation of sterically less hindered siliranium ion is followed by its SN2 opening by the internal nitrogen nucleophile. Oxidative cleavage of σC-Si bond leads to the formation of 3-hydroxypyrrolidines.
Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis
Melgar-Fernandez, Roberto,Gonzalez-Olvera, Rodrigo,Olivares-Romero, J. Luis,Gonzalez-Lopez, Vianney,Romero-Ponce, Leticia,Ramirez-Zarate, Maria Del Refugio,Demare, Patricia,Regla, Ignacio,Juaristi, Eusebio
, p. 655 - 672 (2008/09/17)
Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
