Novel chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to imines

Wang, Min‐Can; Liu, Lantao; Hua, Yuan‐Zhao; Zhang, Junsong; Shi, Yanyan; Wang, Dekun

doi:10.1016/j.tetasy.2005.06.005

Cited by 39 publications

(12 citation statements)

References 57 publications

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“…8 Wang reported the application of both enantiomers of PPFA to the Cu-catalyzed addition of diethylzinc to imines 8 (Scheme 3). 9 Optimization of the reaction conditions found that excellent yields and enantioselectivities could be achieved at room temperature with a variety of aryl groups tolerated on the imine.…”

Section: Introductionmentioning

confidence: 99%

P,N ligands in asymmetric catalysis

2014

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Section: Introductionmentioning

confidence: 99%

P,N ligands in asymmetric catalysis

2014

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“…Corresponding amines 2 were isolated in high yields (75-95%) and high enantiomeric purities (84-92% ee) (Scheme 1). 24 Palladium-catalysed Suzuki cross-coupling between aryl halides 3 and arylboronates 4 proceeded enantioselectively when a PPFA ligand (L1) was used. Axially chiral binaphthyl products 5 were obtained in up 85% ee (Scheme 2).…”

Section: Ferrocene Pn Bidentate Ligandsmentioning

confidence: 99%

Ferrocene phosphane-heteroatom/carbon bidentate ligands in asymmetric catalysis

et al. 2014

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Chiral ferrocene derivatives belong to privileged ligand classes for asymmetric transition metal catalysed reactions. Hetero-bidentate phosphane ligands are hybrid ligands, which combine the properties of phosphorus with those of other donor atoms. This feature creates further asymmetry around the metal centre, which may be helpful for increasing the stereoinduction. Therefore, hetero-bidentate ligands are useful alternatives to homo-bidentate ligands. Ligands featuring phosphorus and nitrogen or sulphur are quite common. From among ferrocene catalysts, ferrocenyl amino phosphanes and phosphane oxazolines serve as excellent examples. Fesulphos and ThioClickFerrophos are notable P,S-ligand examples. On the other hand, combinations of phosphorus with oxygen or carbon are only beginning to show their potential in asymmetric catalysis. Another useful feature in ligands of this type is the markedly different coordination properties of donor atoms, resulting in interesting opportunities for catalysis. Ferrocenyl MOP-analogues or a fascinating combination of phosphane and secondary phosphane-oxide would represent this ligand class. The last section of the review focuses on phosphanes combined with carbon-based donor atoms that are phosphane-alkene and phosphane-carbene ligands. This review focuses on the applications of these hetero-bidentate ferrocene ligands in asymmetric catalysis with a special emphasis on the most recent and influential literature reports.

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“…Inspired by the pioneering work of Tomioka and co‐workers,205 who reported excellent yields and enantiocontrol (typically above 90 % ee ) in the Cu II ‐catalyzed addition of diethylzinc to N ‐tosylimines of aromatic aldehydes with the proline‐based amidophosphine ligand XIV (Table 7, entry 1), Wang and co‐workers have developed a related proline‐derived ferrocenyl amidophosphine ligand ( 57 ; Table 7, entries 2 and 3), but encountered inferior results (79–86 % ee ) in the same transformation 206. On the other hand, moderate to high enantioselectivities (up to 97 % ee ) were attained in the addition of diethylzinc to N ‐phosphinoyl imines using Cu(OTf) 2 /ppfa ( 48 ) as the catalyst system (Table 7, entries 4 and 5) 207…”

Section: Asymmetric Metal‐mediated Additions To Carbonyl Compoundsmentioning

confidence: 99%

Recent Applications of Chiral Ferrocene Ligands in Asymmetric Catalysis

2006

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Despite the impressive progress achieved in asymmetric catalysis during the last decade, an increasing number of new catalysts, ligands, and applications are reported every year to satisfy the need to embrace a wider range of reactions and to improve the efficiency of existing processes. Because of their availability, unique stereochemical aspects, and wide variety of coordination modes and possibilities for the fine-tuning of the steric and electronic properties, ferrocene-based ligands constitute one of the most versatile ligand architectures in the current scenario of asymmetric catalysis. Over the last few years ferrocene catalysts have been successfully applied in an amazing variety of enantioselective processes. This Review documents these recent advances, with special emphasis on the most innovative asymmetric processes and the development of novel, efficient types of ferrocene ligands.

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Novel chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to imines

Cited by 39 publications

References 57 publications

P,N ligands in asymmetric catalysis

P,N ligands in asymmetric catalysis

Ferrocene phosphane-heteroatom/carbon bidentate ligands in asymmetric catalysis

Recent Applications of Chiral Ferrocene Ligands in Asymmetric Catalysis

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