The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium-Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines

被引：16

作者：

Kang, Bo ^{[1
]}

Zhang, Qi-Ying ^{[1
]}

Qu, Gui-Rong ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 10期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; chiral carbocyclic nucleosides; allylic amination; alicyclic MBH adducts; METHYLENECYCLOPROPANE ANALOGS; STEREOSELECTIVE-SYNTHESIS; ANTIVIRAL ACTIVITY; POTENT; DERIVATIVES; INHIBITOR; 1592U89; LIGAND;

D O I：

10.1002/adsc.202000088

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The enantioselective synthesis of carbocyclic nucleosides through the palladium-catalyzed asymmetric allylic amination of alicyclic Morita-Baylis-Hillman (MBH) adducts with purines was successfully developed. With a combination of Pd-2 (dba)(3)/L7 as catalyst, various optically active carbocyclic nucleosides featuring a C=C double bond in the carbocycle moiety were obtained in high yields (up to 97%) with excellent N-9/N-7-selectivities (> 95/5) and enantioselectivities (up to > 99.6%). In addition, these nucleoside analogs allowed for rapid transformation to a variety of other interesting structurally diverse chiral carbocyclic nucleosides.

引用

页码：1955 / 1960

页数：6

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