21034-34-4Relevant academic research and scientific papers
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.
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.
Heteroatom-directed Wacker oxidations. A protection-free synthesis of (-)-heliophenanthrone
Mukherjee, Parag,Sarkar, Tarun K.
supporting information; experimental part, p. 3060 - 3065 (2012/05/07)
The first enantioselective six-step synthesis of (-)-heliophenanthrone has been achieved without any protection-deprotection protocol at an overall yield of 28%. Key features of this synthesis comprise a heteroatom-directed Wacker oxidation of an internal cyclic olefin in addition to asymmetric Brown allylation and ring closing metathesis (RCM). The Royal Society of Chemistry 2012.
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 (2007/10/03)
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
"Me3Al-TMSOSO2CF3" a new reagent for conversion of carbonyl to geminal dimethyl functionality: Regiospecific synthesis of alkylated a ring of arotinoids
Kim, Choung Un,Misco, Peter F.,Luh, Bing Y.,Mansuri, Muzammil M.
, p. 3017 - 3020 (2007/10/02)
Regiospecific synthesis of alkylated A ring of arotinoids has been achieved by using Me3Al-TMSOSO2CF3 as a key reagent for conversion of carbonyl to a geminal dimethyl functionality.
ELECTRON-TRANSFER PROCESSES. NEW SYNTHESIS OF γ-LACTONES BY PEROXYDISULFATE OXIDATION OF ISOPROPYLBENZENES AND ALIPHATIC CARBOXYLIC ACIDS
Giordano, Claudio,Belli, Aldo,Citterio, Attilio,Minisci, Francesco
, p. 3559 - 3562 (2007/10/02)
A new synthesis of γ-lactones by peroxydisulfate oxidation of isopropylbenzenes is described.Evidence concerning the free-radical mechanism is reported; the intermediate formation of alkyl and benzyl radicals is evidenced by trapping them with quinoxaline.The role of the iron catalyst is discussed.
