Regio- and Enantioselective Synthesis of Chiral Pyrimidine Acyclic Nucleosides via Rhodium-Catalyzed Asymmetric Allylation of Pyrimidines

被引：33
|
作者：
Liang, Lei [1 ]
Xie, Ming-Sheng [2 ]
Qin, Tao [2 ]
Zhu, Man [2 ]
Qu, Gui-Rong [2 ]
Guo, Hai-Ming [1 ,2 ]
机构：
[1] Henan Normal Univ, Sch Environm, Xinxiang 453007, Henan, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drugs Innovat, Xinxiang 453007, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 19期
基金：
中国国家自然科学基金;
关键词：
TERMINAL ALLENES; ALLYLIC AMINATION; ALKYNES; REGIODIVERGENT; HYDROAMINATION; PHOSPHONATES; 2-PYRIDONES; DERIVATIVES; IMIDAZOLE; MITSUNOBU;
D O I：
10.1021/acs.orglett.7b02482
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct route to branched N-allylpyrimidine analogues is herein reported via the highly regio- and enantioselective asymmetric allylation of pyrimidines with racemic allylic carbonates. With [Rh(COD)Cl](2)/chiral diphosphine as the catalyst, a range of chiral pyrimidine acyclic nucleosides could be obtained under neutral conditions in good yields (up to 95% yield) with high levels of regio- and enantioselectivities (15:1 to >40:1 B/L and up to 99% ee). Furthermore, chiral pyrimidine acyclic nucleoside bearing two adjacent chiral centers has been successfully synthesized by asymmetric dihydroxylation.
引用
收藏
页码：5212 / 5215
页数：4
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