Category: 1428537-19-2

Mei, Tian-Sheng; Patel, Harshkumar H.; Sigman, Matthew S. published the artcile< Enantioselective construction of remote quaternary stereocentres>, Name: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is trisubstituted alkenyl alc arylboronic acid palladium relay Heck arylation; aryl carbonyl compound quaternary carbon substituted stereoselective preparation.

Small mols. that contain all-carbon quaternary stereocenters-carbon atoms bonded to four distinct carbon substituents-are found in many secondary metabolites and some pharmaceutical agents. The construction of such compounds in an enantioselective fashion remains a long-standing challenge to synthetic organic chemists. In particular, methods for synthesizing quaternary stereocenters that are remote from other functional groups are underdeveloped. Here we report a catalytic and enantioselective intermol. Heck-type reaction of trisubstituted-alkenyl alcs. with aryl boronic acids. This method provides direct access to quaternary all-carbon-substituted β-, γ-, δ-, ε- or ζ-aryl carbonyl compounds, because the unsaturation of the alkene is relayed to the alc., resulting in the formation of a carbonyl group. The scope of the process also includes incorporation of pre-existing stereocenters along the alkyl chain, which links the alkene and the alc., in which the stereocenter is preserved. The method described allows access to diverse mol. building blocks containing an enantiomerically enriched quaternary center.

Nature (London, United Kingdom) published new progress about Alkenyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Name: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Allen, Jamie R.; Bahamonde, Ana; Furukawa, Yukino; Sigman, Matthew S. published the artcile< Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction>, SDS of cas: 1428537-19-2, the main research area is indolylalkanal chemoselective enantioselective preparation; chemoselective enantioselective aza Wacker reaction allylic homoallylic alc indole; enantioselective alkylation indole allylic homoallylic alc palladium catalyst; stereochem mechanism aza Wacker reaction deuterated allylic alc indole.

In the presence of Pd(MeCN)2(OTs)2 and a nonracemic pyridinyloxazoline, 3-substituted indoles such as 3-phenylindole underwent intermol., chemoselective, and enantioselective alkylation/aza-Wacker reactions with cis-allylic and cis-homoallylic alcs. such as (Z)-EtCH:CHCH2OH mediated by p-benzoquinone in 1,2-dichloroethane to yield nonracemic β- and γ-(1-indolyl)alkanals such as I; enamines generated under other conditions were not formed. The mechanism was studied using the reaction of a deuterium-labeled allylic alc.; the stereochem. of the product supported a syn amino-palladation mechanism for the reaction.

Journal of the American Chemical Society published new progress about Alcohols, homoallylic Role: RCT (Reactant), RACT (Reactant or Reagent). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, SDS of cas: 1428537-19-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ma, Teng; Chen, Yate; Li, Yuxiu; Ping, Yuanyuan; Kong, Wangqing published the artcile< Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes>, Recommanded Product: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is nickel catalyzed enantioselective reductive aryl monofluoroalkenylation alkene; aryl bromide gem difluoroalkene monofluoroalkenylation; oxindole monofluoroalkenyl substituent preparation.

Enantioselective Ni-catalyzed reductive aryl monofluoroalkenylation of alkenes between aryl bromides and gem-difluoroalkenes has been developed. The reaction proceeding under room temperature and base-free reaction conditions tolerates a wide range of functional groups on both coupling partners. Various synthetically useful oxindoles containing monofluoroalkenyl substituent are obtained in good yields with 85%-95% enantiomeric excess. In addition, the synthetic method can be further applied to the late-stage monofluoroalkenylation of complex biol. active compounds

ACS Catalysis published new progress about Alkenylation (monofluoro-). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Recommanded Product: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Chun; Santiago, Celine B.; Kou, Lei; Sigman, Matthew S. published the artcile< Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems>, Quality Control of 1428537-19-2, the main research area is arylboronic acid unsaturated carbonyl enantioselective regioselective arylation Heck; aryl unsaturated carbonyl stereoselective preparation.

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional anal. tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

Journal of the American Chemical Society published new progress about Arylation, stereoselective (regioselective). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Quality Control of 1428537-19-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wang, Zhaobin; Yang, Ze-Peng; Fu, Gregory C. published the artcile< Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides>, Category: pyridine-derivatives, the main research area is nickel catalytic enantioconvergent nucleophilic substitution tertiary alkyl electrophiles alkenylzirconium.

The development of efficient methods, particularly catalytic and enantioselective processes, for the construction of all-carbon quaternary stereocentres is an important (and difficult) challenge in organic synthesis due to the occurrence of this motif in a range of bioactive mols. One conceptually straightforward and potentially versatile approach is the catalytic enantioconvergent substitution reaction of a readily available racemic tertiary alkyl electrophile by an organometallic nucleophile; however, examples of such processes are rare. Here we demonstrate that a nickel-based chiral catalyst achieves enantioconvergent couplings of a variety of tertiary electrophiles (cyclic and acyclic α-halocarbonyl compounds) with alkenylmetal nucleophiles to form quaternary stereocentres with good yield and enantioselectivity under mild conditions in the presence of a range of functional groups. These couplings, which probably proceed via a radical pathway, provide access to an array of useful families of organic compounds, including intermediates in the total synthesis of two natural products, (-)-eburnamonine and madindoline A.

Nature Chemistry published new progress about Alkenylation catalysts, stereoselective. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Chun; Tutkowski, Brandon; DeLuca, Ryan J.; Joyce, Leo A.; Wiest, Olaf; Sigman, Matthew S. published the artcile< Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters>, Safety of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is alkenyl aldehyde ketone preparation enantioselective diastereoselective; allylic alkenol alkenyl triflate redox relay Heck palladium catalyst.

An enantioselective, redox-relay Heck alkenylation of trisubstituted allylic alkenol substrates with alkenyl triflates was developed to afford alkenyl aldehydes/ketones e.g., I. This process enabled the construction of vicinal stereocenters in high diastereo- and enantioselectivity and allowed the formation of enolizable α-carbonyl methyl-substituted stereocenters with no observed epimerization under the reported reaction conditions.

Chemical Science published new progress about Alkenals Role: SPN (Synthetic Preparation), PREP (Preparation). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Safety of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Guo, Zi-Qiong; Xu, Hui; Wang, Xing; Wang, Zhen-Yu; Ma, Biao; Dai, Hui-Xiong published the artcile< C3-Arylation of indoles with aryl ketones via C-C/C-H activations>, Application In Synthesis of 1428537-19-2, the main research area is arylindole preparation regioselective; indole aryl ketone arylation palladium catalyst carbon hydrogen activation.

C3-Arylation of indoles with aryl ketones is accomplished via palladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Chemical Communications (Cambridge, United Kingdom) published new progress about Aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1428537-19-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Khan, Ismat Ullah; Kattela, Shivashankar; Hassan, Abbas; Correia, Carlos Roque Duarte published the artcile< Enantioselective total synthesis of the highly selective sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a non-activated cyclopentene-fused spiro-pyrrolidinone>, Application of C13H15F3N2O, the main research area is stereoselective Heck Matsuda desymmetrization cyclopentene fused spiropyrrolidinone arenediazonium tetrafluoroborate; enantioselective total synthesis VPC01091.

A novel, efficient and enantioselective Heck-Matsuda desymmetrization of non-activated cyclopentene-fused spiro-pyrrolidinones was developed. The reaction provided the Heck products in good to excellent yields and selectivities and tolerated a variety of functional groups in arenediazonium tetrafluoroborates (12 examples) with respect to its electronics and substitution patterns. This methodol. was successfully applied in the concise enantioselective total synthesis of VPC01091 (I), a drug candidate for the treatment of multiple sclerosis.

Organic & Biomolecular Chemistry published new progress about Desymmetrization. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application of C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pan, Qi; Ping, Yuanyuan; Wang, Yifan; Guo, Ya; Kong, Wangqing published the artcile< Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes>, Formula: C13H15F3N2O, the main research area is nickel catalyzed ligand controlled regiodivergent reductive dicarbofunctionalization alkene; five six membered benzo fused lactam preparation alkene dicarbofunctionalization; cyclization cross coupling indoleone dihydroquinolinone preparation.

Transition-metal-catalyzed dicarbofunctionalization of alkenes involving intramol. Heck cyclization followed by intermol. cross-coupling has emerged as a powerful engine for building heterocycles with sterically congested quaternary carbon centers. However, only exo-cyclization/cross-coupling products can be obtained; endo-selective cyclization/cross-coupling has not been reported yet and still poses a formidable challenge. We herein report the first example of catalyst-controlled dicarbofunctionalization of alkenes for the regiodivergent synthesis of five- and six-membered benzo-fused lactams bearing all-carbon quaternary centers. Using a chiral Pyrox- or Phox-type bidentate ligand, 5-exo cyclization/cross-couplings proceed favorably to produce indole-2-ones in good yields with excellent regioselectivity and enantioselectivities (up to 98% ee). When C6-carboxylic acid-modified 2,2′-bipyridine was used as the ligand, 3,4-dihydroquinolin-2-ones were obtained in good yields through 6-endo-selective cyclization/cross-coupling processes. This transformation is modular and tolerant of a variety of functional groups. The ligand rather than the substrate structures precisely dictates the regioselectivity pattern. Moreover, the synthetic value of this regiodivergent protocol was demonstrated by the preparation of biol. relevant mols. and structural scaffolds.

Journal of the American Chemical Society published new progress about Alkenylation. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem