Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions

Feng, Xiujuan; Wei, Bowen; Yang, Jing; Du, Haifeng

doi:10.1039/c1ob05971h

Cited by 35 publications

(13 citation statements)

References 52 publications

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“…An easily accessible analogue of 94 (ligand 95), which was first synthesised by Ellman et al, 188 was also applied in the 1,4addition reaction (Table 3, Entry 22). 189 65 Fig. 66 Sulfinamide-alkene hybrid ligands Ligand 94 was employed by the group in two additional catalytic applications.…”

Section: Rhodium Catalysed 14-addition Reactionsmentioning

confidence: 99%

“…An easily accessible analogue of 94 (ligand 95), which was first synthesised by Ellman et al, 188 was also applied in the 1,4-addition reaction (Table 3, entry 22). 189 Ligand 94 was employed by the group in two additional catalytic applications. Firstly, for the kinetic resolution of Morita-Baylis-Hillman adducts by 1,4-addition/b-hydroxy elimination.…”

Section: Rhodium Catalysed 14-addition Reactionsmentioning

confidence: 99%

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The emergence of sulfoxides as efficient ligands in transition metal catalysis

2015

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Sulfoxides are capable of forming stable complexes with transition metals and there have been many comprehensive studies into their binding properties. However, the use of sulfoxides, particularly chiral sulfoxides, as ligands in transition metal catalysis is rather less well developed. This review aims to describe these catalytic studies and covers new developments that are showing very promising results and that have led to a renewed interest in this field.

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Section: Rhodium Catalysed 14-addition Reactionsmentioning

confidence: 99%

Section: Rhodium Catalysed 14-addition Reactionsmentioning

confidence: 99%

The emergence of sulfoxides as efficient ligands in transition metal catalysis

2015

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“…These chiral S/olefin ligands were successfully applied in Rh-catalyzed asymmetric 1,2or 1,4-additions, and formal [3+2] cycloadditions, giving the desired products with high levels of reactivity and enantioselectivity (Figure 2). [13]…”

Section: Chiral Olefin Hybrid Ligandsmentioning

confidence: 99%

Chiral Dienes: From Ligands to FLP Catalysts

Feng

Meng

2022

Chin. J. Chem.

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Comprehensive SummaryOlefins are very easily accessible compounds which are both popular substrates in synthetic chemistry and good ligands in the organometallic complexes. This dual character makes olefins a rich source of chiral ligands and catalysts for asymmetric catalysis. Herein, we will briefly summarize our studies on the development of chiral diene ligands for transition‐metal catalyzed asymmetric reactions and chiral FLP catalysts for asymmetric metal‐free hydrogenations and hydrosilylations. Several acyclic chiral diene ligands as well as P/olefin and S/olefin hybrid ligands were developed for Rh or Pd‐catalyzed asymmetric reactions. With these ligands in hand, we further put forward a novel strategy for acquiring chiral FLP catalysts via the in situ hydroboration of chiral dienes with Piers’ borane. These catalysts proved to be highly effective for asymmetric metal‐free hydrogenations and hydrosilylations of imines, silyl enol ethers, ketones, and aromatic N‐heterocycles. What is the most favorite and original chemistry developed in your research group?The development of acyclic dienes both as chiral ligands and as precursors of chiral FLP catalysts.How do you get into this specific field? Could you please share some experiences with our readers?When I started my independent research in 2008, chiral olefins belong to one novel ligand type. We got into the field with the thought of the simpler the better. This experience further led us to step into FLP catalysis.What is the most important personality for scientific research?Courage and persistence of doing something unique.What are your hobbies?Walking and playing cards.How do you keep balance between research and family?Life is not only research, but also family. You believe it, the balance is there.What is your favorite journal(s)?My favorite journal is Organic Letters, in which authors can publish their work rapidly and readers can browse the progress of organic chemistry comprehensively.

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“…Metal-catalyzed conjugated addition reactions of carbon nucleophiles to α,β-unsaturated compounds are the most widely used reactions for asymmetric carbon-carbon bond formation [ 1 , 2 , 3 ]. Much interest has recently been shown in rhodium-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ] using various ligands [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ] such as biaryl bisphosphines [ 4 , 5 , 6 , 7 , 8 ], phosphoramidites [ 22 , 23 , 24 , 25 , 26 , 27 , 28 ], diphosphonite [ 29 ], amidomonophosphines [ 30 , 31 ], N -heterocyclic carbenes [ 32 , 33 ], P-chiral phosphine [ 34 ], and dienes [ 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ,…”

Section: Introductionmentioning

confidence: 99%

“…Although many chiral ligands give adducts with good selectivity for cyclic enones, there are few ligands that give good results for both acyclic and cyclic enones. In addition, though conjugate addition of ortho -substituted arylboronic acids to α,β-unsaturated cyclic enones has been achieved in high enantioselectivities [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 21 , 44 ], there have been few reports on this reaction for acyclic enones [ 38 , 51 , 52 ]. On the other hand, we have already reported that a new bidentate phosphoramidite ligand (Me-BIPAM) based on O -linked-BINOL was synthesized and that a rhodium/Me-BIPAM complex was a better catalyst than several monodentate phosphoramidites for conjugate addition of arylboronic acids to α,β-unsaturated cyclic and acyclic carbonyl compounds [ 53 , 54 ].…”

Section: Introductionmentioning

confidence: 99%

An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones

et al. 2012

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The process of any contact lens related keratitis generally starts with the adhesion of opportunistic pathogens to contact lens surface. This article focuses on identifying the factors which have been reported to affect bacterial adhesion to contact lenses. Adhesion to lenses differs between various genera/species/strains of bacteria. Pseudomonas aeruginosa, which is the predominant causative organism, adheres in the highest numbers to both hydrogel and silicone hydrogel lenses in vitro. The adhesion of this strain reaches maximum numbers within 1h in most in vitro studies and a biofilm has generally formed within 24 h of cells adhering to the lens surface. Physical and chemical properties of contact lens material affect bacterial adhesion. The water content of hydroxyethylmethacrylate (HEMA)-based lenses and their iconicity affect the ability of bacteria to adhere. The higher hydrophobicity of silicone hydrogel lenses compared to HEMA-based lenses has been implicated in the higher numbers of bacteria that can adhere to their surfaces. Lens wear has different effects on bacterial adhesion, partly due to differences between wearers, responses of bacterial strains and the ability of certain tear film proteins when bound to a lens surface to kill certain types of bacteria.

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Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions

Cited by 35 publications

References 52 publications

The emergence of sulfoxides as efficient ligands in transition metal catalysis

The emergence of sulfoxides as efficient ligands in transition metal catalysis

Chiral Dienes: From Ligands to FLP Catalysts

An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones

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