Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

被引：130
作者：
Cheng, Lei [1 ,2 ]
Li, Ming-Ming [1 ,2 ]
Xiao, Li-Jun [1 ,2 ]
Xie, Jian-Hua [1 ,2 ,3 ]
Zhou, Qi-Lin [1 ,2 ,3 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 37期
基金：
中国国家自然科学基金;
关键词：
PALLADIUM-CATALYZED ADDITION; ALLYLIC ALKYLATIONS; CARBONYL-COMPOUNDS; ALPHA-ALKYLATION; ACTIVE METHYLENE; ALKYNES; ALLENES; PRONUCLEOPHILES; ALLYLATION; DIENES;
D O I：
10.1021/jacs.8b09346
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful y,delta-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of (R)-flobufen.
引用
收藏
页码：11627 / 11630
页数：4
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