通过β-核苷碱基取代丙烯酸酯的高对映选择性1,3-偶极环加成反应快速且多样地合成手性氮杂环核苷类似物。

A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates.

作者信息

Yang Qi-Liang, Xie Ming-Sheng, Xia Chao, Sun Huan-Li, Zhang Dan-Jie, Huang Ke-Xin, Guo Zhen, Qu Gui-Rong, Guo Hai-Ming

机构信息

Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

出版信息

Chem Commun (Camb). 2014 Dec 7;50(94):14809-12. doi: 10.1039/c4cc06632d.

DOI:10.1039/c4cc06632d

PMID:25319349

Abstract

A rapid and divergent access to chiral azacyclic nucleoside analogues has been established via highly exo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with β-nucleobase substituted acrylates. Using 1 mol% of a chiral copper complex, various chiral azacyclic nucleoside analogues were obtained in high yields, excellent exo-selectivities and enantioselectivities (98 to >99% ee).

摘要

通过甲亚胺叶立德与β-核苷碱基取代的丙烯酸酯的高度外型选择性和对映选择性1,3-偶极环加成反应，已建立了一种快速且多样的手性氮杂环核苷类似物的合成方法。使用1 mol%的手性铜配合物，可高产率、高外型选择性和对映选择性（98%至>99% ee）地获得各种手性氮杂环核苷类似物。