113194-59-5Relevant academic research and scientific papers
Chiral ligand control in enantioselective reduction of ketones by SmI2 for ketyl radical addition to olefins
Mikami, Koichi,Yamaoka, Makoto
, p. 4501 - 4504 (1998)
Samarium(II) diiodide-mediated reductive coupling of ketones with α,β- unsaturated esters is shown to afford enantioselectively γ-butyrolactones by the addition of 2,2'-bis(diphenylphosphinyl)-1,1'-binaphthyl (BINAPO) as a chiral ligand.
Chemo- and Regioselective Synthesis of Arylated γ-Valerolactones from Bio-based Levulinic Acid with Aromatics Using H-β Zeolite Catalyst
Gundekari, Sreedhar,Srinivasan, Kannan
, p. 1102 - 1111 (2019)
Catalytic coupling of biomass-based molecules to value-added chemical intermediates is an interesting area in biomass research. Arylated γ-valerolactones (Agvls), promising pharmaceutical intermediates that have significant biological activity, are primar
Chemospecificity in arylations of δ- and γ-ketocarboxylic acids with P2O5-MsOH, TfOH, and related acidic media
Yonezawa, Noriyuki,Koike, Masayuki,Kameda, Asami,Naito, Shin,Hino, Tetsuo,Maeyama, Katsuya,Ikeda, Tomiki
, p. 3169 - 3180 (2002)
Remarkable contrast between chemospecificities in acid-mediated arylation of δ- and γ-ketocarboxylic acids was revealed: in the presence of P2O5-MsOH, TfOH, PPA, and MsOH, arylation of δ-ketocarboxylic acid 1A with arenes takes place
Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate
Yoshimura, Tomoyuki,Umeda, Yuki,Takahashi, Risako,Matsuo, Jun-Ichi
, p. 1220 - 1225 (2020/12/17)
The nitrolactonization of alkenyl carboxylic acids mediated by Fe(NO3)3·9H2O has been developed. Nitrolactones were obtained in up to 93% yield by treatment of alkenyl carboxylic acids with Fe(NO3)3·9H2O. Mechanistic studies disclosed that the reaction proceeded through a radical intermediate generated from addition of NO2 to alkenyl carboxylic acids.
ZnI2/Zn(OTf)2-TsOH: A versatile combined-Acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization
Chou, Ting-Hung,Yu, Bo-Hung,Chein, Rong-Jie
supporting information, p. 13522 - 13525 (2019/11/14)
A mild and efficient combined-Acid system using a zinc(ii) salt [ZnI2 or Zn(OTf)2] and p-Toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five-and six-membered O-and N-containing saturated heterocyclic compounds, tetrahydronaphthalene derivatives and polycyclic skeletons in excellent yield with perfect Markovnikov selectivity and under mild conditions. The operational simplicity, broad applicability, and use of inexpensive commercially available catalysts make this protocol superior to existing methodologies.
Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko
, p. 1143 - 1156 (2017/02/18)
The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.
Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D
Ha, Tu M.,Chatalova-Sazepin, Claire,Wang, Qian,Zhu, Jieping
supporting information, p. 9249 - 9252 (2016/08/05)
A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords γ-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of (±)-sacidumlignan D.
Studies on Aromatic Sesquiterpenes. XIII. Synthesis of Lacinilene A and Its Structural Isomer
Tanaka, Juichi,Miyake, Takashi,Iwasaki, Noboru,Adachi, Kazuo
, p. 2851 - 2853 (2007/10/02)
Lacinilene A (6-norcadalen-7-ol) was synthesized from anisole through 6-norcalamenen-7-ol. 6-Nordaucalen-7-ol was also synthesized.
