Category: 152140-65-3

Trost, Barry M.; Schaeffner, Benjamin; Osipov, Maksim; Wilton, Donna A. A. published the artcile< Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect>, COA of Formula: C54H42N2O2P2, the main research area is stereoselective decarboxylative allylic alkylation keto ester palladium catalyst.

The palladium-catalyzed decarboxylative asym. allylic alkylation of β-keto esters is reported. This reaction was applied to the synthesis of (-)-ranirestat. It was expanded to β-keto esters by using allyl chloroformate to form allyl enol carbonates in situ. Two sets of reaction conditions were developed to fine-tune the enantioselectivity.

Angewandte Chemie, International Edition published new progress about Allylic alkylation (decarboxylative, stereoselective). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, COA of Formula: 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

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

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

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

Trost, Barry M.; Tang, Weiping published the artcile< Migratory Hydroamination: A Facile Enantioselective Synthesis of Benzomorphans>, Recommanded Product: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is benzomorphan alkaloid asym preparation; diastereoselective cycloisomerization benzomorphan alkaloid asym preparation; migratory hydroamination benzomorphan alkaloid asym preparation; asym allylic alkylation benzomorphan alkaloid asym preparation.

A highly efficient, general strategy for the enantioselective synthesis of benzomorphans (45-46% overall yield from com. available material) is described. The new synthesis demonstrates the effectiveness of an unprecedented diastereoselective cycloisomerization via migratory hydroamination and the power of palladium-catalyzed asym. allylic alkylation (AAA) of simple ketone enolates in the context of complex synthesis. The strategy outlined here for the enantioselective synthesis of three contiguous stereogenic centers and the novel cycloisomerization should have many applications in alkaloid synthesis.

Journal of the American Chemical Society published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Recommanded Product: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

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

Trost, Barry M.; Xie, Jia published the artcile< Palladium-Catalyzed Diastereo- and Enantioselective Wagner-Meerwein Shift: Control of Absolute Stereochemistry in the C-C Bond Migration Event>, Related Products of 152140-65-3, the main research area is palladium catalyzed Wagner Meerwein ring expansion diastereoselective enantioselective; cyclopentanone derivative diastereoselective enantioselective synthesis.

Inducing absolute stereochem. in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a π-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochem. of both the π-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochem. outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an α-chiral O-tertiary center which has various synthetic applications.

Journal of the American Chemical Society published new progress about Absolute configuration (of ring expansion products). 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

Trost, Barry M.; Xu, Jiayi; Reichle, Markus published the artcile< Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates>, Quality Control of 152140-65-3, the main research area is tertiary hydroxy aldehyde enantioselective preparation; enolate asym allylic alkylation palladium catalysis; oxybutynin formal synthesis synthon.

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chem. A catalytic asym. synthesis of α-tertiary hydroxyaldehydes, e.g. I, via palladium-catalyzed asym. allylic alkylation of siloxy enol carbonates, e.g. II and III, with excellent yields and enantioselectivity, is reported. Its synthetic utility is demonstrated in the formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

Journal of the American Chemical Society published new progress about Aldehydes, hydroxy 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, Quality Control 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

Das, Mrinal K.; Kumar, Nivesh; Bisai, Alakesh published the artcile< Catalytic Asymmetric Total Syntheses of Naturally Occurring Amarylidaceae Alkaloids, (-)-Crinine, (-)-epi-Crinine, (-)-Oxocrinine, (+)-epi-Elwesine, (+)-Vittatine, and (+)-epi-Vittatine>, Quality Control of 152140-65-3, the main research area is asym catalytic total synthesis Amaryllidaceae alkaloid; crinine catalytic asym total synthesis decarboxylative allylation; epi crinine catalytic asym total synthesis decarboxylative allylation; oxocrinine catalytic asym total synthesis decarboxylative allylation; elwesine epi catalytic asym total synthesis decarboxylative allylation; vittatine catalytic asym total synthesis decarboxylative allylation.

An expeditious approach to catalytic enantioselective total syntheses of crinine-type Amaryllidaceae alkaloids has been accomplished via a Pd-catalyzed enantioselective decarboxylative allylation of allylenol carbonates as a key step (up to 96% ee). Using this strategy, collective total syntheses of Amaryllidaceae alkaloids such as (-)-epi-elwesine I (R = OH, R1 = R2 = H), (-)-crinine I (R = H, R1 = OH, R22 = bond), (-)-epi-crinine I (R = OH, R1 = H, R22 = bond), (-)-oxocrinine I (RR1 = O, R22 = bond), and (-)-buphanisine I (R = H, R1 = OH, R22 = bond) have been accomplished. Gratifyingly, naturally occurring Amaryllidaceae alkaloids such as (+)-vittatine II (R = OH, R1 = H, R22 = bond), (+)-epi-vittatine II (R = H, R1 = OH, R22 = bond), and (+)-epi-elwesine II (R = R2 = H, R1 = OH) have also been achieved by switching the antipode of the ligand used in the catalytic enantioselective step.

Organic Letters published new progress about Allylation catalysts, stereoselective (decarboxylative). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Quality Control 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

Tintas, Mihaela-Liliana; Azzouz, Rabah; Peauger, Ludovic; Gembus, Vincent; Petit, Emilie; Bailly, Laetitia; Papamicael, Cyril; Levacher, Vincent published the artcile< Access to Highly Enantioenriched Donepezil-like 1,4-Dihydropyridines as Promising Anti-Alzheimer Prodrug Candidates via Enantioselective Tsuji Allylation and Organocatalytic Aza-Ene-Type Domino Reactions>, SDS of cas: 152140-65-3, the main research area is enantioenriched donepezil dihydropyridine preparation anti Alzheimer activity; enantioselective Tsuji allylation organocatalysis aza ene domino.

This work aims at exploiting both the enantioselective Tsuji allylation of allyl carbonate and an organocatalytic aza-ene-type domino reaction between enal and β-enaminone to develop a straightforward access to all of the four possible stereoisomers of a donepezil-like 1,4-dihydropyridine (er up to 99.5:0.5; overall yield up 64%), an anti-Alzheimer’s prodrug candidate. This strategy was extended to the preparation of other enantioenriched 1,4-dihydropyridines (eight examples), highlighting its potential in the development of these chiral AChE inhibitors.

Journal of Organic Chemistry published new progress about Allylation (Tsuji). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, SDS of cas: 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

Valli, Matteo; Bruno, Paolo; Sbarbada, Davide; Porta, Alessio; Vidari, Giovanni; Zanoni, Giuseppe published the artcile< Stereodivergent Strategy for Neurofuran Synthesis via Palladium-Catalyzed Asymmetric Allylic Cyclization: Total Synthesis of 7-epi-ST-Δ8-10-Neurofuran>, Computed Properties of 152140-65-3, the main research area is neurofuran synthesis asym allylic cyclization.

An enantioselective stereodivergent approach to two key neurofuran precursors, belonging to the AC and ST classes, has been developed starting from a single achiral precursor. The absolute configuration of the THF cores was secured by a Pd-catalyzed asym. allylic alkylation. From the ST precursor, 7-epi-ST-Δ8-10-neurofuran (I) was prepared

Journal of Organic Chemistry published new progress about Allylic alkylation, stereoselective. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Computed Properties 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