Category: chiral-phosphine-ligands

Recommanded Product: 210169-54-3In 2016 ,《Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines》 appeared in Journal of the American Chemical Society. The author of the article were Kubota, Koji; Watanabe, Yuta; Hayama, Keiichi; Ito, Hajime. The article conveys some information:

We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theor. study of the reaction mechanism is also described. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Recommanded Product: 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Recommanded Product: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Zhang, Jinyu; Yan, Nuo; Ju, Cheng-Wei; Zhao, Dongbing published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Nickel(0)-Catalyzed Asymmetric Ring Expansion Toward Enantioenriched Silicon-Stereogenic Benzosiloles》.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

The development of a straightforward strategy to obtain enantioenriched silicon-stereogenic benzosiloles remains a challenging yet appealing synthesis venture due to their potential future application in chiral electronic and optoelectronic devices. In this context, all of the existing methods rely on Rh-catalyzed systems and are somewhat limited in scope. Herein, we disclose the first Ni0-catalyzed ring expansion process that enables the preparation of benzosiloles possessing tetraorganosilicon stereocenters in excellent yields and enantioselectivities. The presented catalysis strategy is further applied to the asym. synthesis of silicon-stereogenic bis-silicon-bridged π-extended systems. Preliminary studies reveal that such compounds exhibit fluorescence emission, Cotton effects and circularly polarized luminescence (CPL) activity. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2016,Kita, Yusuke; Hida, Shoji; Higashihara, Kenya; Jena, Himanshu Sekhar; Higashida, Kosuke; Mashima, Kazushi published 《Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins》.Angewandte Chemie, International Edition published the findings.Electric Literature of C38H28O4P2 The information in the text is summarized as follows:

Efficient rhodium(III) catalysts were developed for asym. hydrogenation of simple olefins. A series of chloride-bridged dinuclear rhodium(III) complexes were synthesized from the rhodium(I) precursor [RhCl(cod)]2, chiral diphosphine ligands, and hydrochloric acid. Complexes from the series acted as efficient catalysts for asym. hydrogenation of (E)-prop-1-ene-1,2-diyldibenzene and its derivatives without any directing groups, in sharp contrast to widely used rhodium(I) catalytic systems that require a directing group for high enantioselectivity. The catalytic system was applied to asym. hydrogenation of allylic alcs., alkenylboranes, and unsaturated cyclic sulfones. Control experiments support the superiority of dinuclear rhodium(III) complexes over typical rhodium(I) catalytic systems. The experimental part of the paper was very detailed, including the reaction process of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Electric Literature of C38H28O4P2)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Electric Literature of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

The author of 《Palladium-Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit》 were Li, Qiankun; Fu, Chunling; Ma, Shengming. And the article was published in Angewandte Chemie, International Edition in 2014. Formula: C50H56O14P2 The author mentioned the following in the article:

In the presence of a nonracemic bis[bis(trimethoxyphenyl)phosphino]biphenyl and bis(allylpalladium chloride) and using DBU in o-xylene, tosylamides RNHTs (R = H2C:CHCH2, Me2C:CHCH2, H2C:CMeCH2, HCCCH2, n-PrCCCH2, H2C:C:CHCH2, PhCH2, Me; Ts = 4-MeC6H4SO2) underwent regioselective and enantioselective substitution reactions with allenylmethyl phosphates H2C:C:CHCHR1OP(:O)(OEt)2 [R1 = BuCH2CH2, Bu, PhCH2CH2, H2C:CH(CH2)8, Cl(CH2)5, THPO(CH2)5, Me3SiCC(CH2)3, n-Pr; THP = tetrahydropyran-2-yl] to give nonracemic allenylmethylamines such as (S)-H2C:C:CHCHR1NRTs [R = H2C:CHCH2, Me2C:CHCH2, H2C:CMeCH2, HCCCH2, n-PrCCCH2, H2C:C:CHCH2, PhCH2, Me; R1 = BuCH2CH2, Bu, PhCH2CH2, H2C:CH(CH2)8, Cl(CH2)5, HO(CH2)5, Me3SiCC(CH2)3, n-Pr] (I) in 47-90% yields and in 88-94% ee. The structure of a nonracemic cyclopentapyridinone dinitrophenylhydrazone derived from I (R = n-PrCCCH2; R1 = BuCH2CH2) in two steps was determined by X-ray crystallog. In addition to this study using (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine], there are many other studies that have used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Formula: C50H56O14P2) was used in this study.

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Formula: C50H56O14P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2009,Chemistry – A European Journal included an article by Hashmi, A. Stephen K.; Hamzic, Melissa; Rominger, Frank; Bats, Jan W.. Electric Literature of C50H56O14P2. The article was titled 《Gold Catalysis: Enantiotopos Selection》. The information in the text is summarized as follows:

The Au-catalyzed enantioselective cycloisomerization of furyldialkynes, e.g. I, for the preparation of phenols, e.g. II, was reported. After reading the article, we found that the author used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Electric Literature of C50H56O14P2)

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Electric Literature of C50H56O14P2 These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

The author of 《Highly enantioselective copper(I)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones》 were Sanz-Marco, Amparo; Blay, Gonzalo; Munoz, M. Carmen; Pedro, Jose R.. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2015. Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene The author mentioned the following in the article:

The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(I)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic center are obtained with good yields and excellent enantioselectivities. The experimental part of the paper was very detailed, including the reaction process of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《The first asymmetric Sonogashira coupling for the enantioselective generation of planar chirality in paracyclophanes》 was written by Kanda, Kazumasa; Koike, Tamami; Endo, Kohei; Shibata, Takanori. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene And the article was included in Chemical Communications (Cambridge, United Kingdom) on April 14 ,2009. The article conveys some information:

The double Sonogashira coupling of diiodoparacyclophanes with alkynes proceeded to give planar chiral dialkynylparacyclophanes. A chiral Pd catalyst, which was prepared in situ from PdCl2(CH3CN)2 and Taniaphos, realized the first asym. Sonogashira coupling with up to ca. 80% ee. In the part of experimental materials, we found many familiar compounds, such as (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Category: chiral-phosphine-ligandsOn October 4, 2017 ,《Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-C2 Symmetric Digold Catalysts》 was published in Journal of the American Chemical Society. The article was written by Garcia-Morales, Cristina; Ranieri, Beatrice; Escofet, Imma; Lopez-Suarez, Laura; Obradors, Carla; Konovalov, Andrey I.; Echavarren, Antonio M.. The article contains the following contents:

The enantioselective intermol. gold(I)-catalyzed [2+2] cycloaddition of terminal alkynes and alkenes was achieved using non-C2-chiral Josiphos digold(I) complexes as catalysts, by the formation of the monocationic complex. This new approach was applied to the enantioselective total synthesis of rumphellaone A. After reading the article, we found that the author used (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8Category: chiral-phosphine-ligands)

(R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Category: chiral-phosphine-ligands These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2020,Chemical Communications (Cambridge, United Kingdom) included an article by Du, Mengyuan; Yu, Longhui; Du, Ting; Li, Zhaokun; Luo, Yueyang; Meng, Xiangyu; Tian, Zhengtao; Zheng, Changwu; Cao, Weiguo; Zhao, Gang. SDS of cas: 286454-86-2. The article was titled 《N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis》. The information in the text is summarized as follows:

An enantioselective Strecker reaction to construct trifluoromethylated quaternary stereocenters with N-PMP and unexplored N-Boc trifluoromethyl ketimines RC(CF3)=NR1 [R = Ph, 3,5-difluorophenyl, thiophen-2-yl, etc.; R1 = 4-methoxyphenyl, C(O)OC(CH3)3] catalyzed using an organophosphine dual-reagent catalyst has been developed. The enantioselectivities of the corresponding products (R/S)-RC(CF3)(CN)NH(R1) with the same catalyst could be switched by using different N-protecting groups (N-PMP or N-Boc). The trifluoromethyl amino nitriles (R/S)-RC(CF3)(CN)NH(R1) were obtained in high yield and high enantioselectivity in a short time and could be easily converted to a variety of useful trifluoromethyl-containing compounds The results came from multiple reactions, including the reaction of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2SDS of cas: 286454-86-2)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.SDS of cas: 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ye, Xiang-Yu; Liang, Zhi-Qin; Jin, Cong; Lang, Qi-Wei; Chen, Gen-Qiang; Zhang, Xumu published an article in 2021. The article was titled 《Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation》, and you may find the article in Chemical Communications (Cambridge, United Kingdom).Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asym. catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asym. hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol. The experimental process involved the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis