210647-41-9Relevant academic research and scientific papers
Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis
Frison, Gilles,Guinchard, Xavier,Marinetti, Angela,Retailleau, Pascal,Smal, Vitalii,Voituriez, Arnaud,Zhang, Zhenhao
supporting information, p. 3797 - 3805 (2020/03/10)
Tethering a metal complex to its phosphate counterion via a phosphine ligand enables a new strategy in asymmetric counteranion-directed catalysis (ACDC). A straightforward, scalable synthetic route gives access to the gold(I) complex of a phosphine displaying a chiral phosphoric acid function. The complex generates a catalytically active species with an unprecedented intramolecular relationship between the cationic Au(I) center and the phosphate counterion. The benefits of tethering the two functions of the catalyst are demonstrated here in a tandem cycloisomerization/nucleophilic addition reaction, by attaining high enantioselectivity levels (up to 97% ee) at an unusually low 0.2 mol % catalyst loading. Remarkably, the method is also compatible with a silver-free protocol.
Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles
Yao, Tuanli,Zhang, Xiaoxia,Larock, Richard C.
, p. 7679 - 7685 (2007/10/03)
The coupling of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles, either catalyzed by AuCl3 or induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions. Various nucleophiles, i
A new synthesis of fungicidal methyl (E)-3 methoxypropenoates
Rossi, Renzo,Bellina, Fabio,Ciucci, Donatella,Carpita, Adriano,Fanelli, Corrado
, p. 7595 - 7614 (2007/10/03)
Several structural analogues of strobilurin A having general formula (E)-18, in which the methyl (E)-3-methoxypropenoate unit is linked to substituted aromatic, alkenyl or cyclopentenyl substrates, have been efficiently and selectively prepared by Pd-catalyzed cross-coupling reactions between (Z)-2-methoxy-1-(methoxycarbonyl)ethenylzinc halides, (Z)-19, and aryl halides, alkenyl halides or triflates or cyclopentenyl triflates, respectively. Compounds (Z)-19, which represent a new class of highly functionalized and stereodefined organozinc derivatives, have been synthesized in very high yield by reaction of THF solutions of easily available methyl (Z)-2-iodo- or (Z)-2-bromo-3-methoxypropenoate, (Z)-8 and (Z)-12, respectively, with an activated Zn/Ag couple in the presence of TMEDA. Compounds (E)-18 synthesized according to this procedure include substances which are known to be able to control agrochemically important fungi as well as derivatives which are able to inhibit the growth of fungi which deteriorate papery materials.
