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：
中国国家自然科学基金; 中国博士后科学基金;
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.
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页数：5
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