872874-17-4Relevant academic research and scientific papers
Understanding the behavior of N-tosyl and N-2-pyridylsulfonyl imines in CuII-catalyzed aza-Friedel - Crafts reactions
Alonso, Ines,Esquivias, Jorge,Gomez-Arrayas, Ramon,Carretero, Juan C.
, p. 6401 - 6404 (2008)
(Chemical Equation Presented) The different behavior of N-tosyl imines and N-(2-pyridyl)-sulfonyl imines in CuII-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrate
A General Asymmetric Formal Synthesis of Aza-Baylis–Hillman Type Products under Bifunctional Catalysis
Frías, María,Carrasco, Ana Cristina,Fraile, Alberto,Alemán, José
supporting information, p. 3117 - 3121 (2017/12/26)
A new organocatalytic strategy for the synthesis of enantioenriched aza-Baylis–Hillman type products via a frustrated vinylogous reaction is presented. This process proceeds under mild conditions with good yields, completed Z/E selectivity and excellent e
Enantioselective copper-aminopyridine-catalyzed aza-Henry reaction with chelating N-(2-pyridyl)sulfonyl imines
Blay, Gonzalo,Escamilla, Ana,Hernandez-Olmos, Victor,Pedro, Jose R.,Sanz-Marco, Amparo
experimental part, p. 441 - 450 (2012/08/08)
This article describes a copper-catalyzed aza-Henry reaction. Copper complexes of camphor-derived aminopyridines catalyze the addition of nitromethane to N-(2-pyridyl)sulfonyl aldimines to give the corresponding β-nitrosulfonamides with good yields and va
Alkylation of aryl N-(2-pyridylsulfonyl)aldimines with organozinc halides: Conciliation of reactivity and chemoselectivity
Esquivias, Jorge,Arrayas, Ramon Gomez,Carretero, Juan Carlos
, p. 9257 - 9260 (2008/12/22)
(Chemical Equation Presented) The best of both worlds: With a coordinating 2-pyridylsulfonyl group as the N-activating group, aromatic aldimines show unprecedented high reactivity towards the direct addition of alkyl zinc bromide reagents in the presence of catalytic amounts of Cu(OTf)2. The reaction combines high reactivity with wide functional-group compatibility to provide ready access to functionalized benzylamines and derivatives (see example). Tf=trifluoromethanesulfonyl.
Lanthanum aryloxide/pybox-catalyzed direct asymmetric mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor
Morimoto, Hiroyuki,Lu, Gang,Aoyama, Naohiro,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 9588 - 9589 (2008/02/13)
Direct catalytic asymmetric Mannich-type reaction of a trichloromethyl ketone as a propionate equivalent donor is described. A new lanthanum aryloxide-iPr-pybox + lithium aryloxide combined catalyst was the most effective, promoting the reaction of N-2-th
A copper(II)-catalyzed aza-friedel-crafts reaction of N-(2-Pyridyl)sulfonyl aldimines: Synthesis of unsymmetrical diaryl amines and triaryl methanes
Esquivias, Jorge,Arrayas, Ramon Gomez,Carretero, Juan C.
, p. 629 - 633 (2007/10/03)
(Chemical Equation Presented) The choice of the (2-pyridyl)sulfonyl moiety as an N-protecting group and Cu(OTf)2/(±)-binap as catalyst system lead to a highly efficient aza-Friedel-Crafts reaction of electron-rich arenes (Ar2-H) and heteroarenes with N-sulfonyl imines. This protocol is also amenable to the synthesis of unsymmetrical triaryl methanes through a second electrophilic aromatic substitution with a different electron-rich arene (Ar3-H; see scheme).
