Tag: M.W=800-1000

Michon, Christophe; Bethegnies, Aurelien; Capet, Frederic; Roussel, Pascal; de Filippis, Arnault; Gomez-Pardo, Domingo; Cossy, Janine; Agbossou-Niedercorn, Francine published the artcile< Catalytic Asymmetric Allylic Alkylation of 3-Arylated Piperidin-2-ones>, HPLC of Formula: 152140-65-3, the main research area is preparation chiral allyl pyrimidine derivative asym alkylation catalysis.

The preparation of optically active lactams from 3-aryl-2-piperidinone is reported. The quaternary carbon stereo-centers were formed using palladium-catalyzed asym. allylic alkylation reactions. The resulting enantio-enriched compounds are useful intermediates for the synthesis and development of neurokinin antagonists.

European Journal of Organic Chemistry published new progress about Alkylation, stereoselective (allylic). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, HPLC of Formula: 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

Franckevicius, Vilius; Cuthbertson, James D.; Pickworth, Mark; Pugh, David S.; Taylor, Richard J. K. published the artcile< Asymmetric Decarboxylative Allylation of Oxindoles>, Computed Properties of 152140-65-3, the main research area is stereoselective palladium catalyzed decarboxylative allylation oxindole allyl ester; oxindole allyl derivative stereoselective preparation; stereoselectivity reversal substituent size facial selectivity allylation.

An asym. decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation 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, 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

Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas published the artcile< Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates>, COA of Formula: C54H42N2O2P2, the main research area is allyl enol carbonate enantioselective regioselective decarboxylative allylic alkylation palladium; ketone homoallylic asym synthesis.

Palladium-catalyzed decarboxylative asym. allylic alkylation (DAAA) of allyl enol carbonates as a highly chemo-, regio-, and enantioselective process for the synthesis of ketones bearing either a quaternary or a tertiary α-stereogenic center has been investigated in detail. Chiral dibenzobarrelene-based diphosphine ligand was found to be optimal in the DAAA of a broad scope of cyclic and acyclic ketones including simple aliphatic ketones with more than one enolizable proton. The allyl moiety of the carbonates has been extended to a variety of cyclic or acyclic disubstituted allyl groups. The mechanistic studies revealed that, similar to the direct allylation of lithium enolates, the DAAA reaction proceeds through an “”outer sphere”” SN2 type of attack on the π-allylpalladium complex by the enolate. An important difference between the DAAA reaction and the direct allylation of lithium enolates is that in the DAAA reaction, the nucleophile and the electrophile were generated simultaneously. Since the π-allylpalladium cation must serve as the counterion for the enolate, the enolate probably exists as a tight-ion-pair. This largely prevents the common side reactions of enolates associated with the equilibrium between different enolates. The much milder reaction conditions as well as the much broader substrate scope also represent the advantages of the DAAA reaction over the direct allylation of preformed metal enolates.

Journal of the American Chemical Society published new progress about Allylic alkylation catalysts, 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

Yoshida, Mariko; Nemoto, Tetsuhiro; Zhao, Zengduo; Ishige, Yuta; Hamada, Yasumasa published the artcile< Enantioselective construction of all-carbon quaternary spirocenters through a Pd-catalyzed asymmetric intramolecular ipso-Friedel-Crafts allylic alkylation of phenols>, Name: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is spirocyclohexadienone enantioselective synthesis; phenol Friedel Crafts allylic alkylation chiral ligand Pd catalyst.

A novel catalytic asym. synthetic method for making spirocyclohexadienones e. g., I with an all-carbon quaternary spirocenter was developed based on the Pd-catalyzed intramol. ipso-Friedel-Crafts allylic alkylation of phenols. When 5 mol % of the Pd catalyst and 12 mol % of (-)-9-NapBN (-) were used, the spirocyclic adduct was obtained with up to 93% ee, albeit with low chem. yield. On the other hand, when using 6 mol% of the Trost ligand (R,R), the spirocyclic adducts were obtained in good yields with up to 89% ee (diastereoselectivity = 9.2:1).

Tetrahedron: Asymmetry published new progress about Allylic alkylation. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Name: 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

Kaiser, Thomas M.; Yang, Jiong published the artcile< Catalytic Enantioconvergent Decarboxylative Allylic Alkylation of Allyl Indolenine-3-carboxylates>, SDS of cas: 152140-65-3, the main research area is indole allyl asym synthesis; indolenine carboxylate allyl preparation enantioconvergent decarboxylative allylic alkylation.

A catalytic enantioconvergent process has been developed for the conversion of racemic allyl indolenine-3-carboxylates I (R1 = H, Cl, Me, MeO; R2 = MeCOCH2CH2, MeCH:CHCH2, PhCH2, 2-naphthylmethyl, etc.; R3 = H2C:CH, MeCH:CH, H2C:CMe) into enantiomerically enriched C3-quaternary indolenines II. A Pd-catalyzed decarboxylative allylic alkylation reaction was employed for both stereoablation of the racemic allyl indolenine-3-carboxylates and enantioselective formation of the quaternary carbon center.

European Journal of Organic Chemistry published new progress about Allylic alkylation catalysts, stereoselective. 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

Starkov, Pavel; Moore, Jared T.; Duquette, Douglas C.; Stoltz, Brian M.; Marek, Ilan published the artcile< Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates>, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is enantioselective preparation acyclic quaternary carbon stereocenter; palladium catalyzed decarboxylative allylic alkylation amide enolate.

Authors report a divergent and modular protocol for the preparation of acyclic mol. frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand.

Journal of the American Chemical Society published new progress about Allylic alkylation (enantioselective). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Safety of 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.; Xu, Jiayi; Schmidt, Thomas published the artcile< Ligand controlled highly regio- and enantioselective synthesis of α-acyloxyketones by palladium-catalyzed allylic alkylation of 1,2-enediol carbonates. [Erratum to document cited in CA149:307451]>, Related Products of 152140-65-3, the main research area is erratum enediol carbonate allyl alkylation palladium catalysis ligand; acetoxyketone asym preparation erratum.

On page 11853, in Table 2, entries 11 and 12, the stereochem. assignments of the cyclohexenyl ring of compound 20 and the cycloheptenyl ring of compound 22 should be S, not R. This assignment is based on the empirical model we proposed (Trost,B.M.; Toste, F.D. J. Am. Chem.Soc. 1999, 121,4545), which has been supported by extensive exptl. data.

Journal of the American Chemical Society published new progress about Alkyl aryl ketones 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

Nemoto, Tetsuhiro; Ishige, Yuta; Yoshida, Mariko; Kohno, Yuta; Kanematsu, Mutsumi; Hamada, Yasumasa published the artcile< Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols>, Application In Synthesis of 152140-65-3, the main research area is stereoselective spirocyclohexadienone preparation intramol Friedel Crafts allylic alkylation; ipso Friedel Crafts intramol alkylation phenol reactant spirocyclohexadienone preparation; palladium catalyzed Friedel Crafts allylic alkylation spirocyclohexadienone preparation.

The first successful Pd-catalyzed intramol. ipso-Friedel-Crafts allylic alkylation of phenols, which provided a new access to spiro[4.5]cyclohexadienones, e.g. I, is described. The present method could be applied to catalytic enantioselective construction of an all-carbon quaternary spirocenter.

Organic Letters published new progress about Diastereoselective synthesis. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Application In Synthesis 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

Akula, Ramulu; Guiry, Patrick J. published the artcile< Enantioselective Synthesis of α-Allyl-α-aryldihydrocoumarins and 3-Isochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation>, COA of Formula: C54H42N2O2P2, the main research area is decarboxylative asym allylation of aryl oxo ester; enantioselective synthesis allyl aryl dihydrocoumarin; isochromanone allyl aryl enantioselective synthesis; crystal structure.

An enantioselective Pd-catalyzed decarboxylative asym. allylic alkylation (DAAA) of α-aryl-β-oxo esters has been developed employing the (R,R)-ANDEN-Ph Trost ligand to prepare a series of α-aryl-α-allyldihydrocoumarins and 3-isochromanones. A variety of aryl groups were successfully employed to afford the dihydrocoumarin and 3-isochromanone products in high yields up to 95% and ee’s up to 96%. Under these conditions, substrates containing di- and mono-o-substituted aryl groups gave the highest levels of enantioselectivities. This work represents the first example of the enantioselective preparation of all-carbon quaternary α-allyl-α-aryl dihydrocoumarins and 3-isochromanones.

Organic Letters published new progress about Allylation catalysts. 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

Trost, Barry M.; Brennan, Megan K. published the artcile< Palladium-Catalyzed Regio- and Enantioselective Allylic Alkylation of Bis Allylic Carbonates Derived from Morita-Baylis-Hillman Adducts>, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is Morita Baylis Hillman adduct regioselective enantioselective allylic alkylation; palladium phosphinonaphthoylaminocyclohexane catalysis regioselective enantioselective allylic alkylation; allylic carbonate regioselective enantioselective allylic alkylation palladium catalysis.

Morita-Baylis-Hillman diene adducts (e.g. (4E)-3-[(ethoxycarbonyl)oxy]-2-methylenehex-4-enoic acid Me ester) were used as substrates in the Pd-catalyzed asym. allylic alkylation reaction with O and C nucleophiles (e.g. p-methoxyphenol) in good regio- and enantioselectivity, e.g. 78 % (88 %ee) (3S,4E)-(+)-3-(4-methoxyphenoxy)-2-methylenehex-4-enoic acid Me ester (>20:1 regioisomers), using Pd2(dba)3, (1S,2S)-1,2-bis[[[2-(diphenylphosphino)naphthalen-1-yl]carbonyl]amino]cyclohexane and tetrabutylammonium triphenyldifluorosilicate as catalyst system in DME at 25°.

Organic Letters published new progress about Allylic alkylation catalysts, stereoselective (regioselective). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Safety of 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