October 2022 | Page 43 of 44 | Chiral phosphine ligands

Brusoe, Andrew T’s team published research in Angewandte Chemie, International Edition in 2011 | 139139-86-9

Angewandte Chemie, International Editionpublished new progress about Allenes 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, COA of Formula: C44H40P2.

Brusoe, Andrew T.; Alexanian, Erik J. published the artcile< Rhodium(I)-Catalyzed Ene-Allene-Allene [2+2+2] Cycloadditions: Stereoselective Synthesis of Complex trans-Fused Carbocycles>, COA of Formula: C44H40P2, the main research area is eneallene allene rhodium catalyzed cycloaddition; hydrindane decalin stereoselective preparation four contiguous stereocenters; fused carbocycle stereoselective preparation.

The rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes was utilized for the construction of a variety of trans-fused hydrindanes and decalins in a highly convergent manner, with three σ bonds, two rings, and up to four contiguous stereocenters generated in a regio- and stereoselective fashion.

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

Senda, Taichi’s team published research in Journal of Organic Chemistry in 2001-10-19 | 139139-86-9

Journal of Organic Chemistrypublished new progress about Addition reaction catalysts, stereoselective. 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Formula: C44H40P2.

Senda, Taichi; Ogasawara, Masamichi; Hayashi, Tamio published the artcile< Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboron Reagents to 5,6-Dihydro-2(1H)-pyridinones. Asymmetric Synthesis of 4-Aryl-2-piperidinones>, Formula: C44H40P2, the main research area is asym synthesis arylpiperidinone; stereoselective addition organoboron pyridinone; paroxetine intermediate stereoselective preparation.

Catalytic asym. synthesis of 4-aryl-2-piperidinones was realized by asym. 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing the 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40°C gave the highest yield of the arylation product with high enantioselectivity (98% ee). The (R)-4-(4-fluorophenyl)-2-piperidinone obtained is a key intermediate for the synthesis of (-)-Paroxetine.

Wiest, Johannes M’s team published research in Angewandte Chemie, International Edition in 2018 | 277306-29-3

Angewandte Chemie, International Editionpublished new progress about [2+2] Cycloaddition reaction (enantioselective, of alkenes and allenoates). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Category: chiral-phosphine-ligands.

Wiest, Johannes M.; Conner, Michael L.; Brown, M. Kevin published the artcile< Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates>, Category: chiral-phosphine-ligands, the main research area is hebelophyllene E sesquiterpene lactone preparation relative configuration; alkene catalytic enantioselective cycloaddition allenoate; chiral geminal dimethylcyclobutane derivatives preparation diastereoselective reduction; oxazaborolidine catalyst enantioselective cycloaddition alkene allenoate; cycloaddition; enantioselectivity; natural products; small ring systems; total synthesis.

The first synthesis of hebelophyllene E (I) is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophyllene E. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and allenoates provides access to the required chiral geminal dimethylcyclobutanes. Key to its success is the identification of a novel oxazaborolidine catalyst which promotes the cycloaddition in high enantioselectivities with good functional-group tolerance (9 examples, up to 97:3 e.r.). Thus, a late-stage cycloaddition using a fully functionalized alkene, followed by a diastereoselective reduction allows a concise entry to this class of natural products.

Tanaka, Ken’s team published research in Tetrahedron in 2008-06-30 | 139139-86-9

Tetrahedronpublished 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.

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.

Felix, Ryan J’s team published research in Nature Chemistry in 2012-05-31 | 325168-88-5

Nature Chemistrypublished new progress about [3,3]-Sigmatropic rearrangement. 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, HPLC of Formula: 325168-88-5.

Felix, Ryan J.; Weber, Dieter; Gutierrez, Osvaldo; Tantillo, Dean J.; Gagne, Michel R. published the artcile< A gold-catalysed enantioselective Cope rearrangement of achiral 1,5-dienes>, HPLC of Formula: 325168-88-5, the main research area is gold catalysis enantioselective cope rearrangement achiral dienes.

Since the discovery of the Cope rearrangement in the 1940s, no asym. variant of the rearrangement of achiral 1,5-dienes has emerged, despite the successes that have been achieved with its heteroatom variants (Claisen, aza-Cope, and so on). This article reports the first example of an enantioselective Cope reaction that starts from an achiral diene. The new gold(I) catalyst derived from double Cl–abstraction of ((S)-3,5-xylyl-PHANEPHOS(AuCl)2), has been developed for the sigmatropic rearrangement of alkenyl-methylenecyclopropanes. The reaction proceeds at low temperature and the synthetically useful vinylcyclopropane products are obtained in high yield and enantioselectivity. D. functional theory calculations predict that: (1) the reaction proceeds via a cyclic carbenium ion intermediate, (2) the relief of strain in the methylenecyclopropane moiety provides the thermodn. driving force for the rearrangement and (3) metal complexation of the transition-state structure lowers the rearrangement barriers.

Lipshutz, Bruce H’s team published research in Journal of the American Chemical Society in 2008-11-05 | 277306-29-3

Journal of the American Chemical Societypublished new progress about Aldol condensation catalysts, stereoselective (intramol.). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Computed Properties of 277306-29-3.

Lipshutz, Bruce H.; Amorelli, Benjamin; Unger, John B. published the artcile< CuH-Catalyzed Enantioselective Intramolecular Reductive Aldol Reactions Generating Three New Contiguous Asymmetric Stereocenters>, Computed Properties of 277306-29-3, the main research area is unsaturated ketone copper enantioselective intramol reductive aldol chiral phosphine; cycloalkanol stereoselective preparation; enantioselective intramol reductive aldol catalyst copper chiral phosphine.

Treatment of β,β-disubstituted-α,β-unsaturated ketones, e.g., I, bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to cycloalkanols, e.g., II, with three newly created adjacent chiral centers. Excellent de’s and ee’s are obtained for several examples studied.

Chang, Xin’s team published research in Angewandte Chemie, International Edition in 2020-05-25 | 139139-93-8

Angewandte Chemie, International Editionpublished new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (bis(alkenyl)dihydrosilanes). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products of 139139-93-8.

Chang, Xin; Ma, Pei-Long; Chen, Hong-Chao; Li, Chuan-Ying; Wang, Peng published the artcile< Asymmetric Synthesis and Application of Chiral Spirosilabiindanes>, Related Products of 139139-93-8, the main research area is alkenyldihydrosilane preparation rhodium catalyzed asym double hydrosilation spirocyclization; spirosilabiindane chiral preparation reaction aminophosphine; phosphoramidite spirosilabiindane chiral preparation catalyst ligand asym hydrogenation carboamination; crystal structure chiral spirosilabiindane diol derivative phosphoramidite; mol structure chiral spirosilabiindane diol derivative phosphoramidite; asymmetric catalysis; ligand design; silanes; spirocompounds; synthetic methods.

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asym. double hydrosilation, for the 1st time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on >10 g scale using this protocol. The potential of this new spirosilabiindane scaffold in asym. catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramol. carboamination.

Tanaka, Ken’s team published research in Synlett in 2007-06-01 | 139139-86-9

Synlettpublished 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, Application of C44H40P2.

Tanaka, Ken; Nishida, Goushi; Sagae, Hiromi; Hirano, Masao published the artcile< Enantioselective synthesis of C2-symmetric dimethyl cyclohexadienedicarboxylates through cationic rhodium(I)/modified-BINAP-catalyzed [2+2+2] cycloadditions>, Application of C44H40P2, the main research area is enediyne enantioselective intramol cycloaddition rhodium BINAP catalyst; diyne fumarate enantioselective cycloaddition rhodium BINAP catalyst; tricyclic cyclohexadienedicarboxylate asym synthesis; bicyclic cyclohexadienedicarboxylate asym synthesis.

A cationic rhodium(I)/(S)-Tol-BINAP complex was employed to catalyze an enantioselective intramol. [2+2+2] cycloaddition of a trans enediyne leading to a C2-sym. tricyclic di-Me cyclohexadienedicarboxylate in 95% yield with 59% ee. A cationic rhodium(I)/(R)-H8-BINAP complex was employed to catalyze an intermol. [2+2+2] cycloaddition of 1,6-diynes with di-Me fumarate leading to C2-sym. bicyclic di-Me cyclohexadienedicarboxylates in 35-96% yields with 82-98% ee.

Seraphim, Thiago V’s team published research in Structure (Oxford, United Kingdom) in 2022-01-06 | 606-68-8

Structure (Oxford, United Kingdom)published new progress about A-kinase anchor protein 4 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, COA of Formula: C21H27N7Na2O14P2.

Seraphim, Thiago V.; Nano, Nardin; Cheung, Yiu Wing Sunny; Aluksanasuwan, Siripat; Colleti, Carolina; Mao, Yu-Qian; Bhandari, Vaibhav; Young, Gavin; Holl, Larissa; Phanse, Sadhna; Gordiyenko, Yuliya; Southworth, Daniel R.; Robinson, Carol V.; Thongboonkerd, Visith; Gava, Lisandra M.; Borges, Julio C.; Babu, Mohan; Barbosa, Leandro R. S.; Ramos, Carlos H. I.; Kukura, Philipp; Houry, Walid A. published the artcile< Assembly principles of the human R2TP chaperone complex reveal the presence of R2T and R2P complexes>, COA of Formula: C21H27N7Na2O14P2, the main research area is chaperone complex Armadillo repeat domain folded protein; AAA+ proteins; ATPases; PAQosome; R2TP; RUVBL1/2; macromolecular complex assembly; molecular chaperones; protein folding.

R2TP is a highly conserved chaperone complex formed by two AAA+ ATPases, RUVBL1 and RUVBL2, that associate with PIH1D1 and RPAP3 proteins. R2TP acts in promoting macromol. complex formation. Here, we establish the principles of R2TP assembly. Three distinct RUVBL1/2-based complexes are identified: R2TP, RUVBL1/2-RPAP3 (R2T), and RUVBL1/2-PIH1D1 (R2P). Interestingly, we find that PIH1D1 does not bind to RUVBL1/RUVBL2 in R2TP and does not function as a nucleotide exchange factor; instead, RPAP3 is found to be the central subunit coordinating R2TP architecture and linking PIH1D1 and RUVBL1/2. We also report that RPAP3 contains an intrinsically disordered N-terminal domain mediating interactions with substrates whose sequences are primarily enriched for Armadillo repeat domains and other helical-type domains. Our work provides a clear and consistent model of R2TP complex structure and gives important insights into how a chaperone machine concerned with assembly of folded proteins into multisubunit complexes might work.

Hato, Yoshio’s team published research in Journal of Organic Chemistry in 2016-09-02 | 139139-93-8

Journal of Organic Chemistrypublished new progress about Alkenynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Safety of (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Hato, Yoshio; Oonishi, Yoshihiro; Yamamoto, Yasunori; Nakajima, Kiyohiko; Sato, Yoshihiro published the artcile< Stereoselective Construction of Spiro-Fused Tricyclic Frameworks by Sequential Reaction of Enynes, Imines, and Diazoalkenes with Rh(I) and Rh(II) Catalysts>, Safety of (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is stereoselective spiro fused tricyclic compound; rhodium catalyst imine tethered enyne reaction diazoalkene.

Stereoselective construction of spiro-fused tricyclic compounds from enynes having a tethered imine with diazoalkenes was achieved by Rh(I)- and Rh(II)-catalyzed sequential reactions. This method consists of three reactions, i.e., Rh(I)-catalyzed cyclization of enynes with a tethered imine, Rh(II)-catalyzed cyclopropanation with diazoalkenes, and Cope rearrangement. Notably, the sequential reactions can be operated in one pot, in which Rh(I) and Rh(II) catalysts work in relay without any serious catalyst deactivation to afford the spirocycles in a stereoselective manner.