- Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
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We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp3)?C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.
- Dong, Xiao-Yang,Du, Xuan-Yi,Fang, Jia-Heng,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Xin-Yuan,Wang, Li-Lei,Xia, Hai-Dong
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supporting information
p. 16926 - 16932
(2020/08/25)
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- Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
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In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
- Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
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supporting information
p. 5699 - 5703
(2019/08/01)
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- Novel compounds that reverse the disease phenotype in Type 2 Gaucher disease patient-derived cells
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Gaucher disease (GD) results from inherited mutations in the lysosomal enzyme β-glucocerobrosidase (GCase). Currently available treatment options for Type 1 GD are not efficacious for treating neuronopathic Type 2 and 3 GD due to their inability to cross the blood-brain barrier. In an effort to identify small molecules which could be optimized for CNS penetration we identified tamoxifen from a high throughput phenotypic screen on Type 2 GD patient-derived fibroblasts which reversed the disease phenotype. Structure activity studies around this scaffold led to novel molecules that displayed improved potency, efficacy and reduced estrogenic/antiestrogenic activity compared to the original hits. Here we present the design, synthesis and structure activity relationships that led to the lead molecule Compound 31.
- Abou-Gharbia, Magid,Childers, Wayne,Colussi, Dennis J.,Fan, Rong,Gordon, John,Jacobson, Marlene A.,Liu, Yuxiao,Martinez, Rogelio,Melenski, Edward
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supporting information
(2019/12/11)
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- PYRETHROID COMPOUND, AND HAIR RESTORER AND HAIR RESTORER COMPOSITION COMPRISING THE SAME
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PROBLEM TO BE SOLVED: To provide a pyrethroid compound having hair growth effect. SOLUTION: The present invention provides a pyrethroid compound represented by general formula (1) [in general formula (1), R1 is selected from a hydrogen atom, a halogen atom, an azido group, an alkoxy group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms, R2 is selected from a methyl group, an ethyl group and an isopropyl group, R3 is selected from -C≡N, -C≡CH, -C≡C-CH3 and -CH=CH2, and R4 is selected from a methyl group, a phenyl group, a 2-methoxy ethyl group, a methoxymethyl group, and a propargyl group]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0035; 0039; 0040
(2017/08/26)
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- NOVEL FUNCTIONALIZED N,N-DIALKYLAMINO PHENYL ETHERS AND THEIR METHOD OF USE
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Pharmaceutical compositions of the invention comprise functionalized N,N-dialkylamino phenyl ethers derivatives having a disease-modifying action in the treatment of diseases associated with lysosomal storage dysfunction that include Gaucher's disease, and any disease or condition involving lysosomal storage dysfunction.
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Paragraph 0294
(2017/12/29)
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- Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries
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A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.
- Stivala, Craig E.,Zakarian, Armen
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supporting information; experimental part
p. 11936 - 11939
(2011/09/19)
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- N-heterocyclic carbene-mediated enantioselective addition of phenols to unsymmetrical alkylarylketenes
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Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering α-alkyl-α-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phe-nylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.
- Concellon, Carmen,Duguet, Nicolas,Smith, Andrew D.
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supporting information; experimental part
p. 3001 - 3009
(2010/03/26)
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- Therapeutic benzazarine compounds
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A method for the treatment of neurological disorders, comprising administering to a mammal in need of such treatment an effective amount of a compound of formula I or of formula II (formulae set out on pages following the Examples), wherein R1/s
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- Process for preparing phenyl-acetic acid esters
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A process for preparing a substituted phenyl-acetic acid ester of the formula (I), SPC1 wherein R1 is an ethyl group or an isopropyl group, R2 is a hydrogen atom, a C1 -C4 alkyl group, a methoxy group, a halogen atom or a methylenedioxy group, which comprises reacting a quaternary ammonium salt of the formula (III), SPC2 wherein X is a halogen atom, and A is an alkylamine, pyridine or an N-alkylaniline, with a carboxylic acid of the formula (II), SPC3 wherein R1 and R2 are each as defined above, its reactive derivative, or a mixture of the acid and its reactive derivative.
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- 2H-2-benzazepin-1,3-diones
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A compound of the formula SPC1 Wherein X and R are as defined hereinafter, at least one of X and R being other than hydrogen, are provided and which are useful as central nervous system stimulants and for inducing increased motor activity as well as in vitro antimicrobial agents.
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