Synthesis of acyclic nucleoside analogues through P(NMe2)3-Mediated regioselective N-alkylation

被引：0

作者：

Huang, Ke-Xin ^{[1
]}

Chen, Zhao-Yang ^{[1
]}

Liu, Xue-Guo ^{[1
]}

Gao, Wen-Chao ^{[2
]}

机构：

[1] Nanyang Inst Technol, Sch Biol & Chem Engn, Nanyang 473000, Henan, Peoples R China

[2] Nanyang Normal Univ, Sch Chem & Pharmaceut Engn, Nanyang 473000, Henan, Peoples R China

来源：

TETRAHEDRON | 2024年 / 162卷

关键词：

Acyclic nucleosides; N-Alkylation; P(NMe2)3-Mediated; ALPHA-KETO ESTERS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; PURINE NUCLEOSIDES; MICHAEL ADDITION; QUINONE METHIDES; FACILE SYNTHESES; 1+4 ANNULATION; BOND;

D O I：

10.1016/j.tet.2024.134126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient approach for synthesizing acyclic nucleoside analogues with a side chain length of two carbon atoms has been established. It involves purines reacting with alpha-keto esters in a P(NMe2)(3)-mediated deoxygenation process, yielding the products in high yields and regioselectivities (22 examples, up to 93 % yield, up to >20:1 N-9/N-7 selectivities). This reaction features short reaction times, metal-free catalysis, mild reaction conditions, and broad substrate scope, all of which make it promising for practical applications.

引用

页数：6

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