Chiral phosphine ligands

James, Jinju; Guiry, Patrick J. published the artcile< Highly Enantioselective Construction of Sterically Hindered α-Allyl-α-Aryl Lactones via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation>, Electric Literature of 152140-65-3, the main research area is enantioselective preparation allyl aryl lactone; palladium catalyst decarboxylative asym allylic alkylation.

Pd-catalyzed decarboxylative asym. allylic alkylation has been developed for sterically hindered α-aryl, β-oxoallyl ester lactone substrates. Pb-mediated α-arylation of the β-oxoallyl ester was used as the key step to synthesize the substrates for catalysis in moderate to high yields. Optimization studies for decarboxylative asym. allylic alkylations (DAAA) were conducted using δ-valerolactone-derived α-aryl β-oxoallyl ester with 2,4,6-trimethoxyphenyl as the aryl substituent. Using (R,R)-ANDEN-Ph Trost as the chiral ligand, enantioselectivities of up to >99% ee and 98% ee were achieved with the six-membered and five-membered lactone substrates, resp. Bulky aryl groups containing di-ortho substitutions and naphthyl groups gave the highest enantioselectivities. This synthetic route allows for the simple modification of aryl groups, giving highly enantioselective access to important structural motifs.

ACS Catalysis published new progress about Allylic alkylation. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Electric Literature of 152140-65-3.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Tanaka, Ken; Takahashi, Maho; Imase, Hidetomo; Osaka, Takuya; Noguchi, Keiichi; Hirano, Masao published the artcile< Enantioselective synthesis of α,α-disubstituted α-amino acids by Rh-catalyzed [2+2+2] cycloaddition of 1,6-diynes with protected dehydroamino acid>, Recommanded Product: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is enantioselective synthesis amino acid rhodium BINAP catalyst cycloaddition diyne; dehydroamino acid cycloaddition diyne catalyst rhodium BINAP.

We have determined that a cationic rhodium(I)/BINAP complex catalyzes a [2+2+2] cycloaddition of 1,6-diynes with protected dehydroamino acids, leading to protected α-amino acids bearing a quaternary carbon center in high yield with high enantioselectivity. Thus, aminoisoindolecarboxylate I (Ts = tosyl) was obtained in 96% yield and 97 ee by cycloaddition reaction of TsN(CH2CCMe)2 with AcNHC(:CH2)CO2Me using Rh(cod)2BF4/(R)-BINAP.

Tetrahedron published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Recommanded Product: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Burns, Alan R.; Lam, Hon Wai; Roy, Iain D. published the artcile< Enantioselective, rhodium-catalyzed 1,4-addition of organoboron reagents to electron-deficient alkenes>, Application of C44H40P2, the main research area is review enantioselective rhodium catalyzed organoboron addition electron deficient alkene.

A review. The enantioselective 1,4-addition of organometallic reagents to electron-deficient alkenes is one of the most important methods for carbon-carbon bond formation. Within this field, the rhodium-catalyzed 1,4-addition of organoboron reagents to electron-deficient alkenes occupies a prominent position owing to (1) the availability, stability, and functional group tolerance of organoboron reagents, (2) the wide range of acceptors that may be employed, (3) the ability of a broad range of structurally distinct families of chiral ligands to induce high enantioselectivities in the reactions, and (4) the usually mild and exptl. convenient conditions, which generally do not require any special precautions to exclude air or moisture.

Organic Reactions (Hoboken, NJ, United States) published new progress about 1,4-Addition reaction catalysts (stereoselective). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Application of C44H40P2.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Yang, Bo; Yang, Wu; Guo, Yonghong; You, Lijun; He, Chuan published the artcile< Enantioselective Silylation of Aliphatic C-H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles>, Category: chiral-phosphine-ligands, the main research area is rhodium catalyzed enantioselective silylation cyclization styrene derivative arylsilane; silicon stereogenic dihydrobenzosilole containing dehydrocholesterol preparation crystal structure; mol structure silicon stereogenic dihydrobenzosilole containing dehydrocholesterol; C(sp3)−H silylation; asymmetric catalysis; dihydrobenzosiloles; hydrosilylation; silanes.

A Rh(I)-catalyzed enantioselective silylation of aliphatic C-H bonds for the synthesis of Si-stereogenic dihydrobenzosiloles is demonstrated. This reaction involves a highly enantioselective intramol. C(sp3)-H silylation of dihydrosilanes, followed by a stereospecific intermol. alkene hydrosilylation leading to the asym. tetrasubstituted silanes. A wide range of dihydrosilanes and alkenes displaying various functional groups are compatible with this process, giving access to a variety of highly functionalized Si-stereogenic dihydrobenzosiloles in good to excellent yields and enantioselectivities.

Angewandte Chemie, International Edition published new progress about Crystal structure. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Category: chiral-phosphine-ligands.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Yoshida, Tomoka; Tajima, Yuki; Kobayashi, Masayuki; Masutomi, Koji; Noguchi, Keiichi; Tanaka, Ken published the artcile< Rhodium-Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides>, Electric Literature of 139139-93-8, the main research area is cycloheptadiene diastereoselective preparation rhodium catalyst reaction mechanism; spiro cyclohexadiene stereoselective preparation rhodium catalyst reaction mechanism; alkyne unsaturated ketone cycloaddition; asymmetric catalysis; cycloaddition; heterocycles; rhodium; synthetic methods.

A cationic rhodium(I)/H8-binap complex catalyzed the [3+2+2] cycloaddition of 1,6-diynes with cyclopropylideneacetamides which produced cycloheptadiene derivatives, e.g., I, through cleavage of cyclopropane rings. A cationic rhodium(I)/(S)-binap complex catalyzed the enantioselective [2+2+2] cycloaddition of terminal alkynes, acetylenedicarboxylates, and cyclopropylideneacetamides which produced spiro-cyclohexadiene derivatives, e.g., II, which retained the cyclopropane rings.

Angewandte Chemie, International Edition published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Seo, Kyeongdeok; Jang, Seok Hyeon; Rhee, Young Ho published the artcile< Sequential Metal Catalysis towards 7-Oxostaurosporine and Its Non-Natural Septanose Analogue>, Related Products of 152140-65-3, the main research area is palladium catalyzed oxidative cyclization bicyclic aminoglycoside septanose oxostaurosporine preparation; septanose oxostaurosporine metal catalysis indolocarbazole alkoxyallene chemoselective addition synthon; Asymmetric synthesis; De novo synthesis; Indolocarbazole; Olefin migration; Total synthesis.

We report sequential metal catalysis towards indolocarbazole glycosides. The signature event is highlighted by (i) Pd0-catalyzed addition of indolocarbazole to alkoxyallene combined with ring-closing-metathesis; (ii) Ru-catalyzed chemoselective olefin migration; (iii) PdII-catalyzed oxidative cyclization to build the bicyclic core structure of the target compounds This approach gave access to both natural pyranose- and non-natural septanose glycosides. A short formal synthesis of 7-oxostaurosporine was achieved via this strategy.

Angewandte Chemie, International Edition published new progress about Aminoglycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Related Products of 152140-65-3.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Webster, Robert; Boyer, Alistair; Fleming, Matthew J.; Lautens, Mark published the artcile< Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution>, Name: (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene, the main research area is oxabicyclic alkene chiral rhodium catalyst amine ring opening; aminotetralin stereoselective preparation regiodivergent resolution; rotigotine stereoselective preparation.

Catalyst-controlled asym. ring opening of racemic oxabicyclic alkene I leads to two readily separable regioisomeric products, both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to the biol. relevant mols. Rotigotine and (S)-8-OH-DPAT in a highly efficient and practical manner.

Organic Letters published new progress about Chiral resolution (regiodivergent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Name: (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Najera, Carmen; de Gracia Retamosa, M.; Sansano, Jose M.; de Cozar, Abel; Cossio, Fernando P. published the artcile< Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions>, Related Products of 139139-93-8, the main research area is polysubstituted proline derivative asym preparation; iminoester maleimide asym dipolar cycloaddition silver BINAP; silver BINAP asym dipolar cycloaddition catalyst.

The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the exptl. observed high enantio- and endo-selectivity through a very asynchronous transition state.

Tetrahedron: Asymmetry published new progress about 1,3-Dipolar cycloaddition reaction, stereoselective. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products of 139139-93-8.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Shintani, Ryo; Takagi, Chihiro; Ito, Tomoaki; Naito, Masanobu; Nozaki, Kyoko published the artcile< Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles by Enantioselective [2+2+2] Cycloaddition>, Name: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is rhodium catalyzed asym synthesis silicon stereogenic dibenzosilole; enantioselective cycloaddition silyl prochiral triyne internal alkyne; germanium stereogenic dibenzogermole preparation; optical property dibenzosilole dibenzogermole; crystal mol structure alkynyl dibenzosilole; asymmetric catalysis; cycloaddition; dibenzosilole; rhodium; silicon.

A rhodium-catalyzed asym. synthesis of silicon-stereogenic dibenzosiloles has been developed through a [2+2+2] cycloaddition of silicon-containing prochiral triynes with internal alkynes. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and the present catalysis is also applicable to the asym. synthesis of a germanium-stereogenic dibenzogermole. Preliminary studies on the optical properties of these compounds are also described.

Angewandte Chemie, International Edition published new progress about Alkynes, internal Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Name: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Holzheimer, Mira; Sinninghe Damste, Jaap S.; Schouten, Stefan; Havenith, Remco W. A.; Cunha, Ana V.; Minnaard, Adriaan J. published the artcile< Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision>, Product Details of C54H42N2O2P2, the main research area is crenarchaeol total synthesis structure revision; macrocyclization total synthesis crenarchaeol; ring closing metathesis total synthesis crenarchaeol; archaea; crenarchaeol; structure revision; tetraether lipid; total synthesis.

Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic mol. in organic geochem. The 66-membered macrocycle possesses a unique chem. structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein, we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.

Angewandte Chemie, International Edition published new progress about Absolute configuration. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Product Details of C54H42N2O2P2.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate