title: Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines.
abstract: With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were obtained in 86-99% yields, >20:1 dr, and 94 → 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when α-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results.
authors: Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.
authors: Dan-Jie
authors: DJ
authors: Zhang
authors: Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.
authors: Ming-Sheng
authors: MS
authors: Xie
authors: Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.
authors: Gui-Rong
authors: GR
authors: Qu
authors: Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.
authors: Yao-Wei
authors: YW
authors: Gao
authors: Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.
authors: Hai-Ming
authors: HM
authors: Guo
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D061565:Cycloaddition Reaction; D004952:Esters; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D009705:Nucleosides; D011687:Purines