Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3+2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines
Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3+2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines
复制标题
通过 9-(2-甲苯磺酰基)-9H-嘌呤的不对称 [3 2] 环加成合成氮杂环核苷类似物
DOI：
10.1021/acs.orglett.6b00108
复制
发表时间：
2016-02-19
期刊：
影响因子：
5.2
通讯作者：
Guo, Hai-Ming
中科院分区：
文献类型：
--
作者：
Zhang, Dan-Jie;Xie, Ming-Sheng;Guo, Hai-Ming
以9-(2-对甲苯磺基)-9H-嘌呤为偶极体，通过铜(I)催化的不对称[3+2]环加成反应，以86-99%的产率合成了一系列具有四个连续立体中心的手性氮杂环核苷，产率分别为>；20：1dr和94->；99%ee。(E)-和(Z)-9-(2-对甲苯磺基)-9H-嘌呤都是合适的偶极体，丰富了氮杂环核苷的结构多样性。此外，当探索α-甲基亚胺酯时，相应的含手性四元立体中心的氮杂环核苷也可以得到很好的结果。
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 alpha-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results.