Enantioselective synthesis of chiral carbocyclic pyrimidine nucleosides via asymmetric cyclopropanation

被引：5

作者：

Wang, Hai-Xia ^{[1
]}

Li, Wen-Peng ^{[1
]}

Xia, Chao ^{[1
]}

Xie, Ming-Sheng ^{[1
]}

Qu, Gui-Rong ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Henan Key Lab Organ Funct Mol & Drug Innovat, Sch Chem & Chem Engn,Minist Educ,Key Lab Green Ch, Xinxiang 453007, Henan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 43期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Cyclopropanation; Enantioselective; Organocatalytic; Pyrimidine nucleoside; PURINE-SUBSTITUTED ACRYLATES; LOWER METHYLENE HOMOLOG; 3+2 CYCLOADDITION; ANALOGS; DIAZOOXINDOLES; DERIVATIVES; OXETANOCIN; ANILIDE;

D O I：

10.1016/j.tetlet.2019.151183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to construct chiral cyclopropyl pyrimidine carbocyclic nucleoside analogues bearing a quaternary center was developed via asymmetric Michael-initiated cyclopropanation. The axis chirality was observed in cyclopropyl pyrimidine carbocyclic nucleoside analogues for the first time, which was caused by the rotationally restricted N-C bond in N-COPh moiety. Using (DHQD)(2)AQN as the organocatalyst, diverse cyclopropyl pyrimidine carbocyclic nucleoside analogues were generated in 76-93% yields and 73-96% ee. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：5

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