- Chiral sulfide - phosphine ligand and preparation method and use thereof
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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.
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Paragraph 0059; 0069; 0079; 0089; 0099; 0109; 0120
(2017/08/25)
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- Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids
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A RhII-catalyzed direct and stereospecific N-H- and N-alkyl aziridination of olefins is reported that uses hydroxylamine-O-sulfonic acids as inexpensive, readily available, and nitro group-free aminating reagents. Unactivated olefins, featuring a wide range of functional groups, are converted into the corresponding N-H or N-alkyl aziridines in good to excellent yields. This operationally simple, scalable transformation proceeds efficiently at ambient temperature and is tolerant towards oxygen and trace moisture.
- Ma, Zhiwei,Zhou, Zhe,Kürti, László
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supporting information
p. 9886 - 9890
(2017/08/08)
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- Enantioselective synthesis of tetrahydrofuran derivatives by sequential henry reaction and iodocyclization of γ,δ-unsaturated alcohols
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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.
- Chen, Li-Yan,Chen, Jia-Rong,Cheng, Hong-Gang,Lu, Liang-Qiu,Xiao, Wen-Jing
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supporting information
p. 4714 - 4719
(2014/08/05)
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- Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions
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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
- Cheng, Hong-Gang,Lu, Liang-Qiu,Wang, Tao,Chen, Jia-Rong,Xiao, Wen-Jing
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supporting information; experimental part
p. 5596 - 5598
(2012/07/03)
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- 2-(p-Tolylsulfinyl)benzyl halides as efficient precursors of optically pure trans-2,3-Disubstituted aziridines
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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
- Arroyo, Yolanda,Meana, Angela,Sanz-Tejedor, M. Ascension,Alonso, Ines,Garcia Ruano, Jose Luis
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experimental part
p. 9874 - 9883
(2010/10/04)
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- Stereoselective control of planar α-dimethylsulfonium benzyl carbanions. Synthesis of optically pure trans-aziridines
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(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
- Arroyo, Yolanda,Meana, Angela,Rodriguez, J. Felix,Sanz-Tejedor, M. Ascension,Alonso, Ines,Ruano, Jose L. Garcia
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experimental part
p. 4217 - 4224
(2009/09/25)
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- Enantioselective ring-opening of aziridines
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A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst
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Page/Page column 15
(2009/02/11)
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- Aminosulf(ox)ides as Ligands for Iridium(I)-Catalyzed Asymmetric Transfer Hydrogenation
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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
- Petra, Danielle G. I.,Kamer, Paul C. J.,Spek, Anthony L.,Schoemaker, Hans E.,Van Leeuwen, Piet W. N. M.
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p. 3010 - 3017
(2007/10/03)
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- Studies on a Chiral (N,P) Ligand Containing a C2-Symmetric Aziridine Unit
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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.
- Tanner, David,Wyatt, Paul,Johansson, Fredrik,Bertilsson, Sophie K.,Andersson, Pher G.
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p. 263 - 268
(2007/10/03)
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- Synthesis of Homochiral Amino Alcohols, Aziridines and Diamines via Homochiral Cyclic Sulphites
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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.
- Lohray, Braj B.,Ahuja, Jaimala R.
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- Thermal and Photoisomerisation of Ion Pairs of the 1,3-Diphenyl-2-aza-allyl Carbanion
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Upon irradiation with white light, the predominant conformation of the 1,3-diphenyl-2-aza-allyl carbanion is changed from trans, trans to cis, trans.The kinetics of the reverse dark reaction have been studied.The loose ion pairs with lithium, sodium, and
- Young, Ronald N.,Ahmad, Muhanad A.
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