30531-69-2Relevant articles and documents
Ruthenium(II)-Catalyzed Homocoupling of Weakly Coordinating Sulfoxonium Ylides via C?H Activation/Annulations: Synthesis of Functionalized Isocoumarins
Zhou, Ming-Dong,Peng, Zhen,Wang, He,Wang, Zhao-Hui,Hao, Da-Jin,Li, Lei
, p. 5191 - 5197 (2019/11/13)
Homocoupling of weakly coordinating sulfoxonium ylides was accomplished via ruthenium (II) catalyzed C?H activation process. This strategy provides a convenient, efficient and step-economic method to access 3-substituted isocoumarins with good functional
Gold(i)-catalyzed C-glycosylation of glycosyl: Ortho -alkynylbenzoates: The role of the moisture sequestered by molecular sieves
Chen, Xiaoping,Wang, Qiaoling,Yu, Biao
supporting information, p. 12183 - 12186 (2016/10/21)
C-Glycosylation of glycosyl ortho-hexynylbenzoates with allyltrimethylsilane or silyl enol ethers could proceed smoothly under the catalysis of Ph3PAuNTf2 to provide the corresponding C-glycosides in high yields and stereoselectivity, wherein the moisture sequestered by the molecular sieves was disclosed to play a critical role in the gold(i)-catalytic cycle.
Mechanistic insights into the gold(I)-Catalyzed activation of glycosyl Ortho -Alkynylbenzoates for Glycosidation
Tang, Yu,Li, Jiakun,Zhu, Yugen,Li, Yao,Yu, Biao
supporting information, p. 18396 - 18405 (2014/01/06)
Anomerization, which involves cleavage and formation of the anomeric C-O bond, is of fundamental importance in the carbohydrate chemistry. Herein, the unexpected gold(I)-catalyzed anomerization of glycosyl ortho-alkynylbenzoates has been studied in detail. Especially, crossover experiments in the presence of an exogenous isochromen-4-yl gold(I) complex confirm that the anomerization proceeds via the exocleavage mechanism, involving (surprisingly) the addition of the isochromen-4-yl gold(I) complex onto a sugar oxocarbenium (or dioxolenium) and an elimination of LAu+ from the vinyl gold(I) complex. The inhibitory effect of the exogenous isochromen-4-yl gold(I) complex when in stoichiometric amount on the anomerization has guided us to disclose an isochromen-4-yl gem-gold(I) complex, which is inactive in catalysis but in equilibrium with the monogold(I) complex and the LAu+ catalyst. The proposed key intermediate in the anomerization, a transient glycosyloxypyrylium species, is successfully trapped via a cycloaddition reaction with n-butyl vinyl ether as a dienophile. SN2-like substitution of the initially formed glycosyloxypyrylium intermediate has then been achieved to a large extent via charging with acceptors in an excess amount to lead to the corresponding glycosides in a stereoselective manner.