Category: 201732-49-2

Rimkus, Audrius;Sewald, Norbert published 《Conjugate addition of organozinc compounds to nitroolefins》. The research results were published in《Synthesis》 in 2004.Recommanded Product: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

Sym. R¹₂Zn [R¹ = Et, NC(CH₂)₃, EtO₂C(CH₂)₃, etc.] or mixed diorganozinc compounds R¹ZnR² (R¹ = n-Bu, cyclohexyl, n-heptyl, etc.; R² = Me₃SiCH₂) smoothly react with a series of nitroolefins R³CH:CR⁴NO₂ [R³ = Ph, MeO₂C, (MeO)₂CH, R⁴ = H; R³ = EtO₂C, R⁴ = Me, Et] in the presence of catalytic amounts of copper(I) salts to provide synthetically versatile nitro compounds R¹R³CHCHR⁴NO₂ in moderate to good yields without racemization (when R¹ is chiral). Simple alkyl groups, functionalized residues, or mixed trimethylsilylmethyl (TMSM) organozinc compounds may be employed for conjugate addition, while the TMSM group is not being transferred. Ipso-Substitution is observed in absence of the copper(I) salt. Enantiomerically pure copper(I) complexes with BINOL based chiral phosphoramidite ligands efficiently catalyze the addition of dialkylzinc compounds to nitroalkenes. In nitro acrylates, the nitroolefin moiety acts as the more powerful Michael acceptor compared to the acrylate moiety. The products can easily be transformed into β²-homoamino acids, compounds of high relevance for different areas of preparative organic chem. And (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) was used in the research process.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Recommanded Product: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rimkus, Audrius;Sewald, Norbert published 《First Synthesis of a β²-Homoamino Acid by Enantioselective Catalysis》. The research results were published in《Organic Letters》 in 2003.Formula: C38H34NO2P The article conveys some information:

The enantioselective conjugate addition of diethylzinc to the activated nitroolefin Me 3-nitropropenoate is efficiently catalyzed by copper(I) complexes with BINOL-based enantiopure phosphoramidite ligands. The nitroolefin moiety acts as the predominant Michael acceptor, giving rise to the unambiguous formation of Me 2-ethyl-3-nitropropanoate. Moderate to excellent enantioselectivities and high chem. yields are obtained. The product can easily be transformed into a β²-homoamino acid, 2-[(tert-butoxycarbonyl)aminomethyl]butanoic acid. And (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) was used in the research process.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Formula: C38H34NO2P

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Versleijen, Jos P. G.;Van Leusen, Albert M.;Feringa, Ben L. published 《Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes》. The research results were published in《Tetrahedron Letters》 in 1999.Computed Properties of C38H34NO2P The article conveys some information:

The asym. copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.’s. High enantioselectivities (e.e.’s up to 92%) were obtained with structurally rigid 3-nitrocoumarins, leading to a new route to optically active β-aryl-nitroalkanes. And (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) was used in the research process.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Computed Properties of C38H34NO2P

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Recommanded Product: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amineIn 1999, Imbos, Rosalinde;Brilman, Mirjan H. G.;Pineschi, Mauro;Feringa, Ben L. published 《Highly Enantioselective Catalytic Conjugate Additions to Cyclohexadienones》. 《Organic Letters》published the findings. The article contains the following contents:

Enantioselective copper phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents (R₂Zn) to several 4,4-disubstituted cyclohexadienones was achieved with diastereomeric ratios of up to 99/1 and enantiomeric excess of up to 99%. A catalyst generated from copper triflate and (S)-N,N-bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine showed high levels of stereoselectivity in the 1,4-addition to sym. dienones. The experimental procedure involved many compounds, such as (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Recommanded Product: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

COA of Formula: C38H34NO2PIn 1999, Imbos, Rosalinde;Brilman, Mirjan H. G.;Pineschi, Mauro;Feringa, Ben L. published 《Highly Enantioselective Catalytic Conjugate Additions to Cyclohexadienones. [Erratum to document cited in CA131:228499]》. 《Organic Letters》published the findings. The article contains the following contents:

The corrected versions of references 10 and 11 are given. To complete the study, the researchers used (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.COA of Formula: C38H34NO2P

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Alexakis, Alexandre;Trevitt, Graham P.;Bernardinelli, Gerald published 《Tandem enantioselective conjugate addition: Electophile trapping reactions. Application in the formation of syn or anti aldols》 in 2001. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.SDS of cas: 201732-49-2 The article mentions the following:

2-Cyclohexen-1-one and 2-cyclohept-en-1-one underwent cupric triflate/phosphoramidate ligand catalyzed enantioselective addition of Et₂Zn to give homochiral zinc enolate intermediates which were trapped by cleavage reactions with acetals and orthoesters to give alkoxy substituted and protected 1,3-dicarbonyl products, resp. Thus, reaction of 2-cyclohexen-1-one in CH₂Cl₂ containing cupric triflate and the phosphoramidate ligand I with Et₂Zn at -30° for 30 min and then with Me₂C(OMe)₂ or HC(OMe)₃ in the presence of F₃B.OEt₂ gave the trans-ethylcyclohexanones II and III, resp. Application of chiral acetals, e.g. diphenyldioxolanes IV (R = Ph, 1-propenyl), to this reaction enabled three contiguous stereocenters and two carbon-carbon bonds to be generated in a tandem, one-pot reaction to give aldol products, e.g. V (R = Ph, allyl). The experimental procedure involved many compounds, such as (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.SDS of cas: 201732-49-2

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wilsily, Ashraf;Fillion, Eric published 《Asymmetric Synthesis of Carboxylic Acid Derivatives Having an All-Carbon α-Quaternary Center through Cu-Catalyzed 1,4-Addition of Dialkylzinc Reagents to 2-Aryl Acetate Derivatives》. The research results were published in《Organic Letters》 in 2008.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

The asym. synthesis of carboxylic acid derivatives having an all-carbon α-quaternary center, e.g. I, has been achieved via copper-catalyzed 1,4-addition of dialkylzinc reagents to aryl acetate derivatives, e.g. II, in the presence of phosphoramidite ligand. High isolated yields and enantioselectivities were obtained. It was demonstrated that the Meldrum’s acid and ester moieties present on the all-carbon quaternary center allow for a wide variety of subsequent transformations, leading to the expedient preparation of succinimides, e.g. III, succinate esters and succinic acids, γ-butyrolactones, and β-amino acid derivatives(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) were involved in the experimental procedure.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Howell, Gareth P.;Minnaard, Adriaan J.;Feringa, Ben L. published 《Asymmetric allylation of aryl aldehydes: studies on the scope and mechanism of the palladium catalyzed diethylzinc mediated umpolung using phosphoramidite ligands》. The research results were published in《Organic & Biomolecular Chemistry》 in 2006.Safety of (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

Using modular, monodentate phosphoramidite ligands, enantioselective palladium catalyzed diethylzinc mediated allylation of aldehydes was achieved. The scope of the asym. C-C bond formation was investigated with respect to nucleophilic and electrophilic components and an alternative reaction mechanism is proposed based on our findings. To complete the study, the researchers used (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Safety of (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis