113641-96-6Relevant articles and documents
Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes
Chen, Yuehua,Deng, Hao,Gao, Xing,Guo, Hongchao,Jiang, Feng,Wang, Wei,Wu, Yongjun,Zhu, Dongyu
supporting information, p. 7158 - 7163 (2020/10/02)
A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.
Photoredox-Catalyzed Decarboxylative Alkylation of Silyl Enol Ethers to Synthesize Functionalized Aryl Alkyl Ketones
Kong, Weiguang,Yu, Changjiang,An, Hejun,Song, Qiuling
supporting information, p. 349 - 352 (2018/01/28)
Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.
Synthesis of β-Amino Ketones by Addition of Aryl Methyl Ketones to Sulfinimines: Application to the Total Synthesis of HPA-12, Norsedamine, and Sedamine
Reddy, Arava Amaranadha,Prasad, Kavirayani R.
, p. 13488 - 13499 (2017/12/26)
Synthesis of β-sulfinamido ketones was accomplished by the addition of silyl enol ethers derived from arylmethyl ketones to chiral sulfinimines in excellent yield and selectivity. Application of the formed β-amino substituted ketones is exemplified in the total synthesis of sphingolipid HPA-12 and the sedamine alkaloids.
Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes
Zhang, Changhe,Lupton, David W.
supporting information, p. 4456 - 4459 (2017/09/11)
An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.
Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Scherbinina, Sofya I.,Fedorov, Oleg V.,Levin, Vitalij V.,Kokorekin, Vladimir A.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 12967 - 12974 (2017/12/15)
A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.
Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones
Ren, Shichao,Feng, Chao,Loh, Teck-Peng
supporting information, p. 5105 - 5109 (2015/05/13)
The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.
Construction of Arene-Fused-Piperidine Motifs by Asymmetric Addition of 2-Trityloxymethylaryllithiums to Nitroalkenes: The Asymmetric Synthesis of a Dopamine D1 Full Agonist, A-86929
Yamashita, Mitsuaki,Yamada, Ken-Ichi,Tomioka, Kiyoshi
, p. 1954 - 1955 (2007/10/03)
The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process wa
A versatile tandem retro-[ 1,4]-Brook rearrangement-condensation reaction of o-bromoacetophenone silyl enol ethers
Comanita, Bogdan M.,Woo, Simon,Fallis, Alex G.
, p. 5283 - 5286 (2007/10/03)
The retro-[1,4]-Brook rearrangement (also referred to as the West or silyl-Wittig rearrangement) has been employed with acetophenone silyl enol ethers to allow regiospecific migration of the silicon from oxygen to the ortho position of the aromatic ring.
Synthesis of Benzocarbacephem and Benzocarbapenem Derivatives by Copper-promoted Intramolecular Aromatic Substitution
Joyeau, Roger,Yadav, Lal D. S.,Wakselman, Michel
, p. 1899 - 1908 (2007/10/02)
Copper-mediated cyclisation of 4-azetidinones and 4-azetidinones proved to be a route to benzocarbacephem and benzocarbapenem derivatives respectively.The effect of functionalities present in the alkyl part of the ring to be formed was considered with regard to cyclisation efficiency and further chemical modifications.Conversion, into halide, of the diastereoisomeric mixture (4R,6S; 4S,6R; 4R,6R; and 4S,6S) of t-butyl 2-hydroxybenzocarbacephem-4'-carboxylate (14f) afforded either the chloride (17a) as racemic diastereoisomers or the fluoride (17c) as a single racemic diastereoisomer.The corresponding free carboxylic acids (18a, c) were designed as inactivators of beta-lactamases.
