133522-23-3Relevant academic research and scientific papers
Chiral sulfide - phosphine ligand and preparation method and use thereof
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Paragraph 0059; 0069; 0079; 0089; 0099; 0109; 0120, (2017/08/25)
The present invention provides a novel chiral thioether-phosphine ligand and a preparation method and application thereof. The ligand is a compound shown as a formula I, or enantiomer, non-enantiomer, racemate, pharmaceutically acceptable salt, hydrate and solvate crystal thereof. R1 is an optionally substituted phenyl, and optionally substituted naphthyl; and R2 is methyl and benzyl. The chiral thioether-phosphine ligand provided by the invention as a copper-catalyzed asymmetric cycloaddition ligand can be directly used to prepare various pyrrolidine compounds with substituted multiple chiral centers.
Enantioselective synthesis of tetrahydrofuran derivatives by sequential henry reaction and iodocyclization of γ,δ-unsaturated alcohols
Chen, Li-Yan,Chen, Jia-Rong,Cheng, Hong-Gang,Lu, Liang-Qiu,Xiao, Wen-Jing
supporting information, p. 4714 - 4719 (2014/08/05)
A sequential one-pot Cu-catalyzed asymmetric Henry reaction and iodocyclization is disclosed. The transformation provides efficient access to biologically and synthetically useful 2,2,5-trisubstituted tetrahydrofuran derivatives. The combination of Cu(OAc)2·H2O with a novel chiral sulfoxide-Schiff base hybrid ligand under mild reaction conditions tolerates a wide range of 4-substituted γ,δ-unsaturated aldehydes, and the subsequent iodocyclization furnishes the corresponding products in generally high yields with excellent enantioselectivities. The products can be easily converted into amines with excellent diastereo- and enantioselectivities.
Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions
Cheng, Hong-Gang,Lu, Liang-Qiu,Wang, Tao,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information; experimental part, p. 5596 - 5598 (2012/07/03)
A new class of chiral sulfoxide-Schiff base ligands has been developed by the rational combination of two privileged chiral backbones. These sulfoxide-Schiff base ligands were found to be highly efficient for Cu-catalyzed asymmetric Henry reactions (up to
2-(p-Tolylsulfinyl)benzyl halides as efficient precursors of optically pure trans-2,3-Disubstituted aziridines
Arroyo, Yolanda,Meana, Angela,Sanz-Tejedor, M. Ascension,Alonso, Ines,Garcia Ruano, Jose Luis
experimental part, p. 9874 - 9883 (2010/10/04)
Aziridination of (R)-N-sulfinylaldimines (aryl, heteroaryl and alkenyl derivatives) with 2-(p-tolyl sulfinyl)benzyl iodide in the presence of sodium hexamethyl disilazide takes place with almost complete control of the stereoselectivity (facial and antil
Stereoselective control of planar α-dimethylsulfonium benzyl carbanions. Synthesis of optically pure trans-aziridines
Arroyo, Yolanda,Meana, Angela,Rodriguez, J. Felix,Sanz-Tejedor, M. Ascension,Alonso, Ines,Ruano, Jose L. Garcia
experimental part, p. 4217 - 4224 (2009/09/25)
(Chemical Equation Presented) (R)-N-Sulfinylimine and (S)-N-sulfinylimine react with the ylide derived from (S)-dimethyl-[2-(p-toluenesulfinyl) phenyl]sulfonium salt, affording trans-2,3-disubstituted aziridines. A complete trans selectivity in low facial
Aminosulf(ox)ides as Ligands for Iridium(I)-Catalyzed Asymmetric Transfer Hydrogenation
Petra, Danielle G. I.,Kamer, Paul C. J.,Spek, Anthony L.,Schoemaker, Hans E.,Van Leeuwen, Piet W. N. M.
, p. 3010 - 3017 (2007/10/03)
A new class of efficient catalysts was developed for the asymmetric transfer hydrogenation of unsymmetrical ketones. A series of chiral N,S-chelates (6-22) was synthesized to serve as ligands in the iridium(I)-catalyzed reduction of ketones. Both formic a
Studies on a Chiral (N,P) Ligand Containing a C2-Symmetric Aziridine Unit
Tanner, David,Wyatt, Paul,Johansson, Fredrik,Bertilsson, Sophie K.,Andersson, Pher G.
, p. 263 - 268 (2007/10/03)
As part of a program on the use of chiral aziridines in asymmetric synthesis and catalysis, the enantiopure (N,P) ligand 1, consisting of a C2-symmetric chiral aziridine and a triarylphosphine unit, was prepared. The synthesis was convergent and efficient, proceeding in five steps and 37% overall yield from 2-bromotoluene. The ligand was designed (a) for a study of the asymmetric Pd-catalyzed allylic substitution reaction, (b) in an attempt to obtain a measure of the trans effect of phosphorus relative to an aziridine nitrogen, and (c) to compare its performance with the corresponding chiral phosphinooxazoline species (computational studies having indicated certain similarities between the two ligand types). However, the new aziridine species did not provide levels of enantioselectivity comparable to those obtained with the phosphinooxazoline analogs, and our results serve to underline once more the difficulties associated with the rational design of ligands for asymmetric catalysis.
Synthesis of Homochiral Amino Alcohols, Aziridines and Diamines via Homochiral Cyclic Sulphites
Lohray, Braj B.,Ahuja, Jaimala R.
, p. 95 - 97 (2007/10/02)
Vicinal diols react with thionyl chloride to give 1,2-cyclic sulphites in quantitative yield, which undergo facile ring opening by lithium azide in dimethylformamide to yield azido alcohols and the latter in turn have been stereoselectively transformed into amino alcohols, aziridines and diamines.
