当前位置: X-MOL 学术Acc. Chem. Res. › 论文详情
Gold(I)-Catalyzed Glycosylation with Glycosyl o-Alkynylbenzoates as Donors
Accounts of Chemical Research ( IF 20.955 ) Pub Date : 2018-01-03 , DOI: 10.1021/acs.accounts.7b00573
Biao Yu

The gold(I) catalytic cycle of the present glycosylation protocol has been fully elucidated. In particular, key intermediates, such as the 1-glycosyloxyisochromenylium-4-gold(I) and isochromen-4-ylgold(I) complexes, have been unambiguously characterized. Exploiting the former glycosyloxypyrylium intermediate, SN2-type glycosylations were realized in specific cases, such as β-mannosylation/rhamnosylation. The protodeauration of the latter vinylgold(I) intermediate has been reported to be critically important for the gold(I) catalytic cycle. Thus, the addition of a strong acid as a cocatalyst can dramatically reduce the required loading of the gold(I) catalyst (down to 0.001 equiv). C-Glycosylation with silyl nucleophiles can proceed catalytically when moisture, which is sequestered by molecular sieves, can serve as the H+ donor for the required protodeauration step. Indeed, the unique mechanism explains the merits and broad applicability of the present glycosylation method and provides a foundation for future developments in glycosylation methodologies that mainly involve improving the diastereoselectivity and catalytic efficiency of glycosylations.
更新日期:2018-01-03

 

分享到
评论: 0
期刊列表
上海交通大学化学化工学院陈刚课题组招聘启事
南方科技大学招聘电子信息材料与器件方向博士后和研究助理教授
【问答】请问在THF、氢氧化钠的条件下,图中自由基中间体能否继续裂解?
2017年中科院JCR分区化学大类列表
试剂库存管理
化合物查询
down
wechat
bug