Asymmetric Benzylic Allylic Alkylation Reaction of 3‐Furfural Derivatives by Dearomatizative Dienamine Activation,Chemistry - A European Journal

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Asymmetric Benzylic Allylic Alkylation Reaction of 3‐Furfural Derivatives by Dearomatizative Dienamine Activation
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-04-06 , DOI: 10.1002/chem.201800585
Xiao-Long He ₁ , Hui-Ru Zhao ₁ , Chuan-Qi Duan ₁ , Xu Han ₁ , Wei Du ₁ , Ying-Chun Chen _{1,

2}

Affiliation

The dearomatizative dienamine‐type ortho‐quinodimethane species are smoothly generated between 2‐alkyl‐3‐furfurals and chiral secondary amine catalysts, which undergo asymmetric benzylic allylic alkylation reactions with 2‐nitroallylic acetates efficiently. A spectrum of densely functionalized 3‐furfural derivatives are delivered in moderate to high yields with good to excellent diastereo‐ and enantioselectivity (up to 98 % yield, >19:1 d.r., >99 % ee). The latent transformations allow the facile production of some enantioenriched architectures, such as 1,1,2,2‐tetraarylethanes and triarylmethanes, which are not easily available from other protocols.

中文翻译：

脱芳香化二烯胺活化的3-糠醛衍生物的不对称苯甲酸烯丙基烷基化反应

脱芳香化的二烯胺型邻喹啉甲烷物质在2-烷基-3-糠醛和手性仲胺催化剂之间平稳生成，它们与2-硝基烯丙基乙酸盐有效地进行了不对称的苄基烯丙基烷基化反应。一系列功能强大的3-糠醛衍生物以中等至高收率提供，具有良好或优异的非对映选择性和对映选择性（最高收率98％，> 19：1 dr，> 99％ ee）。潜在的转化使得可以轻松生产一些对映体富集的体系结构，例如1,1,2,2-四芳基乙烷和三芳基甲烷，这是其他协议中不容易获得的。

更新日期：2018-04-06

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