Binaphthyl-based chiral sulfonimide (CSI) is demonstrated for the first time to be an efficient, strong Brønsted acid in asymmetric organocatalysis. A series of CSIs were synthesized and screened in the asymmetric Friedel-Crafts alkylation of indoles with imines. Good to excellent yields and enantioselectivities have been achieved. It was proved that it was crucial to wash the CSI catalyst with HCl before use.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jo2011335 | DOI Listing |
J Chromatogr A
May 2022
Universidad de Alcalá, Departamento de Química Analítica, Química Física e Ingeniería Química, Ctra. Madrid-Barcelona Km. 33.600, Alcalá de Henares, Madrid 28871, Spain; Universidad de Alcalá, Instituto de Investigación Química Andrés M. del Río, Ctra. Madrid-Barcelona Km. 33.600, Alcalá de Henares, Madrid 28871, Spain. Electronic address:
In this study, new chiral ionic liquids based on the non-protein amino acid L-carnitine as cationic chiral counterpart and several anions (bis(trifluoromethane)sulfonimide (NTf), L-lactate or Cl) as counterions were synthesized. Moreover, three different salts based on L-carnitine were also synthesized and the other three were commercially acquired and used for comparison. The synthesized ionic liquids and salts were characterized by nuclear magnetic resonance, fourier transform infrared spectroscopy, high-performance liquid chromatography-mass spectrometry, and elemental analysis.
View Article and Find Full Text PDFChem Sci
August 2019
Department of Chemistry , Indian Institute of Technology Bombay, Powai , Mumbai 400076 , India . Email:
Hypercoordinate iodine has evolved as an impressive class of catalysts for various organic transformations. Extension of this idea to asymmetric applications, such as in the asymmetric difunctionalization of styrene or its derivatives, constitutes an important reaction. In this study, the mechanism and origin of stereoinduction in styrene diamination, with a sulfonimide (HNMs) as the diaminating agent and iodoresorcinol (((iPr)N(CO)-CH(Me)-O)Ar-I) based chiral hypercoordinate iodine as the catalyst, are investigated using density functional theory calculations.
View Article and Find Full Text PDFMolecules
November 2015
Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, Finland.
Chiral tertiary and quaternary amine solvating agents for NMR spectroscopy were synthesized from the wood resin derivative (+)-dehydroabietylamine (2). The resolution of enantiomers of model compounds [Mosher's acid (3) and its n-Bu₄N salt (4)] (guests) by (+)-dehydroabietyl-N,N-dimethylmethanamine (5) and its ten different ammonium salts (hosts) was studied. The best results with 3 were obtained using 5 while with 4 the best enantiomeric resolution was obtained using (+)-dehydroabietyl-N,N-dimethylmethanaminium bis(trifluoromethane-sulfonimide) (6).
View Article and Find Full Text PDFJ Chromatogr A
November 2013
Department of Analytical Chemistry, China Pharmaceutical University, Nanjing 210009, China.
Recently, chiral ionic liquids (ILs) have drawn more and more attention in chiral separation by capillary electrophoresis (CE). In this paper, two chiral ILs based on amino acid derivatives, L-alanine and L-valine tert butyl ester bis (trifluoromethane) sulfonimide, were applied for the first time in CE to evaluate their potential synergistic effects with classical chiral selectors (β-cyclodextrin derivatives) for enantiomeric separation. As observed, improved separation of tested drug enantiomers was obtained with the presence of chiral ILs compared to the conventional β-cyclodextrin derivatives separation system.
View Article and Find Full Text PDFJ Org Chem
October 2013
Graduate School of Engineering, Nagoya University, and ‡Japan Science and Technology Agency (JST), CREST, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
We developed a practical synthesis of optically pure 3,3'-diaryl-1,1'-binaphthyl-2,2'-disulfonic acids (i.e., (R)- or (S)-3,3'-Ar2-BINSAs) from the parent chiral sulfonimides via stepwise N-S bond cleavage of the sulfonimides and the resultant sulfonamides.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!