B(C6F5)3-Catalyzed One-Pot Tandem Diastereoselective Synthesis of cis-2,3-Disubstituted 1,2,3,4-Tetrahydroquinoxalines and cis-2,4-Disubstituted 2,3,4,5-Tetrahydro-1H-1,5-benzodiazepines

被引：4

作者：

Luo, Zhenli ^{[1
]}

Yang, Ji ^{[1
]}

Yao, Zhen ^{[1
]}

Yang, Jianbo ^{[1
]}

Xu, Lijin ^{[1
]}

Shi, Qian ^{[2
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 20期

基金：

中国国家自然科学基金;

关键词：

B(C6F5)(3); 1,2,3,4-tetrahydroquinoxaline; 2,3,4,5-tetrahydro-1,5-benzodiazepine; Hydrosilylation; 1,2-diaminobenzene; 1,2-diketone; 1,3-diketone; STEREOSELECTIVE TRANSFER HYDROGENATION; ASYMMETRIC TRANSFER HYDROGENATION; CATALYZED TRANSFER HYDROGENATION; N-HETEROCYCLES; ENANTIOSELECTIVE REDUCTION; SILYLATIVE REDUCTION; QUINOXALINES; TETRAHYDROQUINOXALINES; HYDROSILYLATION; EFFICIENT;

D O I：

10.1002/adsc.202300817

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

B(C6F5)(3)-catalyzed one-pot tandem cyclization/hydrosilylation of easily accessible 1,2-diaminobenzenes and 1,2- and 1,3-diketones with polymethylhydrosiloxane (PMHS) has been developed for step-economic diastereoselective synthesis of cis-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines and cis-2,4-disubstituted 2,3,4,5-tetrahydro-1H-1,5-benzodiazepines. This metal-free catalytic protocol provides access to various differently substituted products in 53-95% yield and with diastereoselectivities ranging from 6:1 to 20:1. The diastereoselectivity strongly depends on the choice of hydrosilane, with PMHS being optimal. The reaction is operationally simple and readily scaled up, and proceeds without exclusion of air and moisture.

引用

页码：3527 / 3534

页数：8

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