4.7 Article

Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems

期刊

ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 2, 页码 353-359

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901294

关键词

1,4-addition; asymmetric reaction; polymer; Rh nanoparticle; beta,gamma-unsaturated alpha-ketoester

资金

  1. Japan Society for the Promotion of Science (JSPS)
  2. MEXT Japan
  3. NEDO
  4. AMED

向作者/读者索取更多资源

Asymmetric 1,4-addition reactions with beta,gamma-unsaturated alpha-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, beta,gamma-unsaturated alpha-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to beta,gamma-unsaturated alpha-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据