Simple 1,2‐Diamine Ligands for Asymmetric Addition of Aryllithium Reagents to Imines

Cabello, Noemı́; Kizirian, Jean‐Claude; Gille, Segolene; Alexakis, Alexandre; Bérnardinelli, Gerald; Pinchard, Laurent; Caille, Jean-Claude

doi:10.1002/ejoc.200500447

Cited by 51 publications

(13 citation statements)

References 58 publications

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“…(R,R)-TMCDA was prepared according to Jacobsen [44] and Alexakis. [45] Column chromatography separations were achieved on silica gel (40-63 μm). Thin layer chromatographies were performed on aluminum-backed plates pre-coated with silica gel (Merck, silica gel 60 F254).…”

Section: Methodsmentioning

confidence: 99%

O‐Isopropylferrocenesulfonate: Synthesis of Polysubstituted Derivatives and Electrochemical Study

et al. 2021

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Few studies have been reported on the synthesis of ferrocenesulfonates up to now. Here, we describe the use of orthodeprotometalation and "halogen dance" reactions to easily reach original derivatives. Further functionalizations using cross-coupling and metal/halogen exchange were also per-formed from iodinated derivatives. Finally, while the electrochemical properties of selected ferrocenesulfonates were evaluated and compared with the corresponding sulfonamide derivatives, halogen bonds were observed at the solid state for iodinated derivatives of ferrocenesulfonates.

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Section: Methodsmentioning

confidence: 99%

O‐Isopropylferrocenesulfonate: Synthesis of Polysubstituted Derivatives and Electrochemical Study

et al. 2021

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“…[22] After a broad survey of nitrogen substituents, the bis-1,2-(dimethylamino) cyclohexane (6) was found to give the best results with a wide range of aromatic and heteroaromatic N-anisylimines in combination with aryl-and heteroaryllithium reagents, of which 1-napththyllithium gave the best selectivities, Scheme 5.…”

Section: Background Enantioselective Organolithium Additions To Iminesmentioning

confidence: 99%

Studies on the Bisoxazoline‐ and (−)‐Sparteine‐Mediated Enantioselective Addition of Organolithium Reagents to Imines

et al. 2008

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The enantioselective addition of organolithium reagents to N-anisyl aldimines promoted by chiral bisoxazolines and (−)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 95.5:4.5 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.

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“…Chloroform was refluxed over CaH 2 and ethyl acetate was refluxed over CaCO 3 and then freshly distilled. N , N , N ′, N ′-tetramethylcyclohexane-1,2-diamine [ 45 ] and 1,4-dimethylpiperazine [ 46 ] were prepared as described previously in the literature. Purification of final products was done by column chromatography performed on silica gel (silica 0.035–0.070 mm 60 Å).…”

Section: Methodsmentioning

confidence: 99%

Novel Palladium(II) Complexes that Influence Prominin-1/CD133 Expression and Stem Cell Factor Release in Tumor Cells

et al. 2017

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New Pd(II) complexes of 1,7-bis(2-methoxyphenyl)hepta-1,6-diene-3,5-dione were synthesized and structurally characterized. The complexes were tested in vitro on human colon and hepatic carcinoma cell lines, normal hepatic cells and hematopoietic progenitor cells. Biological tests proved that Pd(II) complexes 1 and 2 (containing a curcumin derivative) exhibit a strong in vitro antitumor effect against the cells derived from human colorectal carcinoma and the hepatic metastasis of a colorectal carcinoma. Complex 1 has an outstanding inhibitory effect against BRAF-mutant colon carcinoma and hepatocarcinoma cell growth; 1 and 2 are both more active than the free ligand and have the capacity to trigger early apoptotic processes. By flow cytometric measurements, an important decrease of prominin-1 (CD133) molecule expression on tumor cells membrane was identified in cell populations subjected to 1 and 2. Quantitative immune enzymatic assay proved restrictions in stem cell factor (SCF) release by treated tumor cells. Although less cytotoxic, the free ligand inhibits the surface marker CD133 expression in hepatocarcinoma cells, and in HT-29 colon carcinoma. The new synthesized Pd(II) complexes 1 and 2 exhibit an important potential through their selective cytotoxic activity and by targeting the stem-like tumor cell populations, which leads to the tumor growth arrest and prevention of metastasis.

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Simple 1,2‐Diamine Ligands for Asymmetric Addition of Aryllithium Reagents to Imines

Cited by 51 publications

References 58 publications

O‐Isopropylferrocenesulfonate: Synthesis of Polysubstituted Derivatives and Electrochemical Study

O‐Isopropylferrocenesulfonate: Synthesis of Polysubstituted Derivatives and Electrochemical Study

Studies on the Bisoxazoline‐ and (−)‐Sparteine‐Mediated Enantioselective Addition of Organolithium Reagents to Imines

Novel Palladium(II) Complexes that Influence Prominin-1/CD133 Expression and Stem Cell Factor Release in Tumor Cells

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