Preparation of ferrocenyl imidazolines using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate

Wang, XueQiang; Xia, Ji‐Bao; Dai, Xiaohu; You, Shu‐Li

doi:10.1007/s11426-009-0161-5

Cited by 9 publications

(4 citation statements)

References 43 publications

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“…Wang et al reported the synthesis of ferrocenyl imidazolines (11) from ferrocenyl carboxylic acids (8) and enantiopure diamines (9) in high yields (Scheme 3). [27] These imidazoline derivatives had been commenced as ligands in transition metal-catalyzed processes. [28] The reaction was initiated by the formation of an intermediate amide (10) from the ferrocene containing carboxylic acid (8) and the diamine (9).…”

Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

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Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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Imidazoline is an important class of compounds found in numerous natural and pharmaceutical products. The compounds are also used as an intermediate in the synthesis of organic molecules. Moreover, chiral imidazolines are widely utilized as organocatalysts to synthesize various natural and synthetic organic compounds. In the past decade, there was an increase in interest in developing new methods to synthesize these imidazoline analogs. Both modification of the previously established methods and the development of new methods are carried out significantly. This review article highlights the progress of the synthesis of imidazoline scaffolds in the last few years (2009-present). The review also described the proposed mechanism illustrated in many of the reports.

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Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

“…Wang et al . reported the synthesis of ferrocenyl imidazolines ( 11 ) from ferrocenyl carboxylic acids ( 8 ) and enantiopure diamines ( 9 ) in high yields (Scheme ) . These imidazoline derivatives had been commenced as ligands in transition metal‐catalyzed processes .…”

Section: Synthesis Of Imidazolinesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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“…Precursors 3aa – 3fc were obtained in good yields from the condensation of 2 with ( R )-BINDPCA 1a – 1e or 1f in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) (1.0 mmol) and 1-hydroxybenzotriazole (1.5 mmol) in N , N -dimethylformamide (DMF). Then precatalysts 4aa – 4ab were synthesized from 3aa – 3ab through imidazoline formation using the Hendrickson’s reagent, while ligand L10 was obtained directly from 3fc in this way in moderate yield. After reduction of 4 with HSiCl 3 and Et 3 N in toluene under reflux, the desired ligands L1 – L9 could be obtained in moderate yields in two steps.…”

Section: Resultsmentioning

confidence: 99%

Chiral Imidazoline–Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions

2011

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Chiral imidazoline−phosphine ligands with a 1,1′-binaphthalene framework have been developed as new types of N,P ligands. The chiral ligand L1 prepared from (R)-(−)-2-(diphenylphosphino)-1,1′-binaphthyl-2′-acid efficiently affects the palladium-catalyzed enantioselective allylic alkylation of 1,3-diarylpropenyl acetate with dimethyl malonate to give the corresponding adducts in excellent yields and enantioselectivities (up to 96% ee), and chiral ligand L9 can be used for the palladium-catalyzed asymmetric allylic monofluoromethylation of 1,3-diphenylpropenyl acetate with 1-fluorobis-(phenylsulfonyl)methane to afford the corresponding product in excellent enantioselectivities (up to 98% ee) and moderate yields under mild conditions. The bidentate N,P-coordination pattern to the Pd atom with ligand L1 has been unambiguously confirmed by X-ray diffraction.

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“…The hindered nature of amide 10 placed an unusual demand on Hendrickson’s phosphonium anhydride reagent for dehydrative cyclization. This reagent has performed well in numerous imidazoline syntheses, typically from less substituted diamine backbones. , Not surprisingly, initial attempts at ambient temperature in dichloromethane resulted in no conversion, and refluxing (40 °C) was similarly ineffective. Only when dichloroethane was used at reflux temperature (83 °C) did conversion occur.…”

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confidence: 99%

Substituted Imidazoline Synthesis: A Diastereo- and Enantioselective aza-Henry Route to a Human Proteasome Modulator

Sprague

Johnston

2020

Org. Lett.

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The first enantio- and diastereoselective synthesis of Tepe’s human proteasome modulator is described. Routes to this and other highly substituted chiral imidazolines generally produce racemic material. Key to the route disclosed here is a gram-scale anti-selective aza-Henry reaction of an α-alkyl α-nitro ester nucleophile, catalyzed by a Bis(Amidine) [BAM] chiral proton complex, delivering the key intermediate in high yield as a single stereoisomer. The adduct is reduced to the amino ester and converted to an imidazoline.

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Preparation of ferrocenyl imidazolines using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate

Cited by 9 publications

References 43 publications

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Chiral Imidazoline–Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions

Substituted Imidazoline Synthesis: A Diastereo- and Enantioselective aza-Henry Route to a Human Proteasome Modulator

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