Alkali-Amide-Catalyzed One-Pot Aminoallylation of Aldehydes with Allylbenzenes

被引：7

作者：

Gu, Yuanyun ^{[1
]}

Wang, Yan-En ^{[2
]}

Yuan, Yaqi ^{[1
]}

Xu, Haodong ^{[1
]}

Lu, Yizhou ^{[1
]}

Zhang, Yufei ^{[1
]}

Xue, Fei ^{[3
]}

Xiong, Dan

Mao, Jianyou ^{[1
]}

机构：

[1] 91599 Nanjing Tech Univ, Sch Chem & Mol Engn, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China

[2] Hebei Agr Univ, Coll Sci, Baoding 071000, Peoples R China

[3] Nanjing Forestry Univ, Inst Mat Phys &Chemistry, Coll Sci, Nanjing 210037, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 11期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; POTASSIUM TERT-BUTOXIDE; 1,4-ADDITION REACTIONS; ASYMMETRIC ALLYLATION; ALLYLIC ALKYLATIONS; DIRECT ARYLATION; PALLADIUM; IMINES; OLEFINS; SODIUM;

D O I：

10.1021/acs.joc.3c00581

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deprotonation of allylbenzene was successfully demonstratedwith a catalytic alkali amide base (NaN-(SiMe3)(2)). The deprotonated allyl anion could be trapped by in situ generated N-(trimethylsilyl) aldimines to provide value-added homoallylicamines (39 examples, 68-98% yields) in a one-pot manner withexcellent liner selectivity. Compared with the previously reportedmethod for the synthesis of homoallylic amines, this method does notneed to use the preinstalled protection groups on the imines, whichneed to be removed after the reaction to obtain the N-H freehomoallylic amine derivatives.

引用

页码：7362 / 7372

页数：11

共 79 条

[11] Asymmetric addition of allylic nucleophiles to imino compounds [J].