55895-92-6Relevant articles and documents
Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O–H Bond Insertion of α-Diazo Esters
Zhang, Yiliang,Yao, Yuan,He, Li,Liu, Yang,Shi, Lei
supporting information, p. 2754 - 2761 (2017/08/23)
A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of α-diazo esters into the O–H bond of carboxylic acids to generate an array of synthetically useful α-hydroxy ester derivatives in good ee (up to 95% ee). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism. (Figure presented.).
Trifluoromethylthiolation and Trifluoromethylselenolation of α-Diazo Esters Catalyzed by Copper
Matheis, Christian,Krause, Thilo,Bragoni, Valentina,Goossen, Lukas J.
supporting information, p. 12270 - 12273 (2016/08/24)
α-Diazo esters are smoothly converted into the corresponding trifluoromethyl thio- or selenoethers by reaction with Me4NSCF3or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α-amino acid derivatives. It is well-suited for the late-stage introduction of trifluoromethylthio or -seleno groups into drug-like molecules.
Construction of All-Carbon Quaternary Centers through Cu-Catalyzed Sequential Carbene Migratory Insertion and Nucleophilic Substitution/Michael Addition
Wang, Chengpeng,Ye, Fei,Wu, Chenggui,Zhang, Yan,Wang, Jianbo
, p. 8748 - 8757 (2015/09/15)
A Cu-catalyzed three-component cross-coupling reaction of terminal alkyne, α-diazo ester, and alkyl halide has been developed. This transformation involves sequent migratory insertion of copper-carbene and nucleophilic substitution, in which a C(sp)-C(sp3) bond and a C(sp3)-C(sp3) bond are formed successively on a carbenic center. Michael addition acceptors can also be employed instead of alkyl halides that enable Michael addition to be an alternative way to build C(sp3)-C(sp3) bond. This transformation represents a highly efficient method for the construction of all-carbon quaternary centers.
