Palladium-Catalyzed Asymmetric Sequential Hydroamination of 1,3-Enynes: Enantioselective Syntheses of Chiral Imidazolidinones

被引：43

作者：

Li, Qiuyu ^{[1
,2
]}

Fang, Xinxin ^{[1
,2
]}

Pan, Rui ^{[1
,2
]}

Yao, Hequan ^{[1
,2
]}

Lin, Aijun ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, Sch Pharm, State Key Lab Nat Med SKLNM, Nanjing 210009, Peoples R China

[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 25期

基金：

中国国家自然科学基金;

关键词：

ANTI-MARKOVNIKOV HYDROAMINATION; INTERMOLECULAR HYDROAMINATION; INTRAMOLECULAR HYDROAMINATION; UNACTIVATED ALKENES; GREEN CHEMISTRY; C-N; ALLENES; ALKYNES; DIAMINATION; DIENES;

D O I：

10.1021/jacs.2c03620

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-catalyzed sequential hydroamination of readily available 1,3-enynes is reported. The redox-neutral process provides an efficient route to synthesize a broad scope of imidazolidinones, thiadiazolidines, and imidazolidines. Asymmetric sequential hydroamination generates a series of synthetically valuable, enantioenriched imidazolidinones. Mechanistic studies revealed that the transformation occurred via an intermolecular enyne hydroamination pathway to give an allene intermediate. Subsequent intramolecular hydroamination of the allene intermediate proceeded under the Curtin-Hammett principle to provide enantioenriched imidazolidinone products.

引用

页码：11364 / 11376

页数：13

共 133 条

[1] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].