17605-06-0Relevant articles and documents
Thermolysis of geminal diazides: Reagent-free synthesis of 3-hydroxypyridines
Erhardt, Hellmuth,Kunz, Kevin A.,Kirsch, Stefan F.
, p. 178 - 181 (2017)
An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β- ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.
Syntheses of both diastereoisomers of 2,8-dioxabicyclo[3.2.1]octane derivatives: Degradation products of Daphniphyllum alkaloids
Kongkathip, Boonsong,Sookkho, Rongsan,Kongkathip, Ngampong,Taylor, Walter C.
, p. 1095 - 1096 (1999)
Both diastereoisomers of 1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane-4-caboxylic acid ester (3, 4) and the 4-hydroxy methyl analogues (5, 6) were synthesised from ethyl acetoacetate and diethyl malonate respectively. The key step of these process involved intramolecular cyclisation using palladium chloride as catalyst.
Efficient Synthesis of butenolide-medium ring ether hybrids by a [3 + 2] cyclization-ring-closing metathesis strategy
Langer, Peter,Eckardt, Tobias,Stoll, Martin
, p. 2991 - 2993 (2000)
A new strategy for the synthesis of bicyclic γ-alkylidenebutenolides, butenolide-medium ring ether hybrids, is reported which involves Me3-SiOTf-catalyzed cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride, Mitsunobu reaction, and subsequent ring-closing metathesis.
A Suite of “Minimalist” Photo-Crosslinkers for Live-Cell Imaging and Chemical Proteomics: Case Study with BRD4 Inhibitors
Pan, Sijun,Jang, Se-Young,Wang, Danyang,Liew, Si Si,Li, Zhengqiu,Lee, Jun-Seok,Yao, Shao Q.
, p. 11816 - 11821 (2017)
Affinity-based probes (AfBPs) provide a powerful tool for large-scale chemoproteomic studies of drug–target interactions. The development of high-quality probes capable of recapitulating genuine drug–target engagement, however, could be challenging. “Mini
Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters
Furuta, Miyu,Ide, Kohta,Tokuyama, Hidetoshi
supporting information, p. 9172 - 9176 (2021/11/13)
A mild photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters in an aqueous medium was developed. The sequential reaction process comprising the intramolecular radical addition of α-bromo-β-keto esters to olefins under photoredox catalysis, and subsequent cyclization to form cyclopropane proceeds in one-pot under exceptionally mild conditions at room temperature in the presence of 2,6-lutidine. A broad range of substrates consisting of various alkenes and both base- and acid-sensitive functionalized esters were feasible under the reaction conditions, resulting in a wide range of functionalized bicyclic cyclopropanes. This journal is
Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro
supporting information, p. 1653 - 1657 (2019/05/29)
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.
One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols
Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 15105 - 15108 (2019/12/26)
Herein, we report the nor-AZADO-catalyzed exhaustive aerobic oxidations of 1,2-diols to α-keto acids. Combining oxidation with transamination using dl-2-phenylglycine led to the synthesis of free α-amino acids (AAs) in one pot. This method enables the rapid and flexible preparation of a variety of valuable unnatural AAs, such as fluorescent AAs, photoactivatable AAs, and other functional AAs for bioorthogonal reactions.
General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides
Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin
supporting information, p. 5679 - 5684 (2019/08/01)
A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.
A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of γ,δ-Unsaturated Ketones
Samadi, Sadaf,Orellana, Arturo
, p. 2472 - 2475 (2016/08/25)
We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium-catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium-catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.
Diastereoselective synthesis of the C17-C30 fragment of amphidinol 3
Rival, Nicolas,Hazelard, Damien,Hanquet, Gilles,Kreuzer, Thomas,Bensoussan, Charlelie,Reymond, Sébastien,Cossy, Janine,Colobert, Fran?oise
supporting information, p. 9418 - 9428 (2013/01/15)
The diastereoselective synthesis of the C17-C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were efficiently controlled by using (+)-(R)-methyl-p-tolylsulfoxide as the unique source of chirality.