1469874-75-6Relevant academic research and scientific papers
TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes
Chen, Heshan,Luo, Xiaosheng,Qiu, Saifeng,Sun, Wengjie,Zhang, Jianbo
, p. 13 - 20 (2017)
A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate. The flexi
Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes
Hosseyni, Seyedmorteza,Smith, Courtney A.,Shi, Xiaodong
supporting information, p. 6336 - 6339 (2016/12/23)
In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity.
Transformation of Glycals into α,β,γ,δ-Conjugated Chirons under Metal-Free Conditions
Madhubabu, Tatina,Yousuf, Syed Khalid,Kusunuru, Anil Kumar,Mukherjee, Debaraj
supporting information, p. 7333 - 7338 (2016/02/19)
A diastereoselective, metal-free, one-pot domino synthetic strategy was developed for the transformation of glycals into new chiral scaffolds. Optimization of the reaction conditions to exclude normal Ferrier products, characterization of the new entities
Zinc mediated activation of terminal alkynes: Stereoselective synthesis of alkynyl glycosides
Tatina, Madhu Babu,Kusunuru, Anil Kumar,Yousuf, Syed Khalid,Mukherjee, Debaraj
supporting information, p. 7900 - 7903 (2015/01/08)
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards an alkynyl zinc reagent obtained from alkynes using zinc dust
Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes
Kusunuru, Anil Kumar,Tatina, Madhubabu,Yousuf, Syed Khalid,Mukherjee, Debaraj
supporting information, p. 10154 - 10156 (2013/10/22)
A highly stereoselective rapid C-glycosylation reaction has been developed between glycal and unactivated alkynes in the presence of coppertriflate and ascorbic acid at low catalyst loading and at room temperature. A wide variety of glycals and aryl acetylenes participate in the reaction smoothly. TfOH generated during the reduction of Cu(OTf)2 by ascorbic acid may be the active catalyst for the glycosylation. The Royal Society of Chemistry 2013.
