Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes,Chemical Science

当前位置： X-MOL 学术 › Chem. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes
Chemical Science ( IF 7.6 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1039/c7sc02757e
Yulong Kuang _{1,

2,

3,

4,

5} , Bin Shen _{1,

2,

3,

4,

5} , Li Dai _{1,

2,

3,

4,

5} , Qian Yao _{1,

2,

3,

4,

5} , Xiaohua Liu _{1,

2,

3,

4,

5} , Lili Lin _{1,

2,

3,

4,

5} , Xiaoming Feng _{1,

2,

3,

4,

5}

Affiliation

A diastereodivergent asymmetric Michael-alkylation reaction between 3-chloro-oxindoles and β,γ-unsaturated-α-ketoesters has been achieved using L-RaPr₂/Sc(OTf)₃ and L-PrPr₂/Mg(OTf)₂ metal complexes as catalysts. Both rel-(1R,2S,3R) and rel-(1S,2S,3R) chiral spiro cyclopropane oxindoles were constructed in good yields, diastereoselectivities and ee values. The diastereodivergent control may originate from different alkylation pathways after the Michael addition, with either intramolecular trapping of the aza-ortho-xylylene intermediate or direct S_N2 substitution.

中文翻译：

使用手性N，N'-二氧化物/金属配合物的非对映异构不对称Michael-烷基化反应

使用L-RaPr ₂ / Sc（OTf）₃和L-PrPr ₂ / Mg（OTf）₂金属配合物实现了3-氯-氧吲哚与β，γ-不饱和α-酮酸酯之间的非对映异构性不对称Michael-烷基化反应作为催化剂。两个相对- （1 - [R，2小号，3 - [R ）和相对- （1小号，2小号，3 - [R）手性螺环丙烷氧吲哚的收率，非对映选择性和ee值均良好。非对映异构控制可能来自迈克尔加成后的不同烷基化途径，可能是氮杂-邻二甲苯基中间体的分子内捕集或直接的S _N 2取代。

更新日期：2017-11-22

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11