Multi-component syntheses of 2-pyrrolines and organocatalytic asymmetric syntheses of functionalized chiral 2-pyrrolines,Organic Chemistry Frontiers

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Multi-component syntheses of 2-pyrrolines and organocatalytic asymmetric syntheses of functionalized chiral 2-pyrrolines
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-30 , DOI: 10.1039/d0qo01267j
Yuan Zhong _{1,

2,

3,

4} , Xiaoqiang Zhao _{1,

2,

3,

4} , Xiaoyun Zhao _{2,

3,

4,

5} , Dan Zhang _{2,

3,

4,

6} , Wenli Li _{2,

3,

4,

6} , Shouhui Wei _{1,

2,

3,

4} , Fanhong Liu _{1,

2,

3,

4} , Jihua Yu _{1,

2,

3,

4} , Guichen Li _{2,

3,

4,

6} , Dandan Wang _{2,

3,

4,

5}

Affiliation

The green and atom-economical synthesis of functionalized 2-pyrrolines has been achieved by carrying out the multi-component tandem [2 + 2 + 1] annulation reaction of simple and commercially available starting materials, namely, an aldehyde, glycine ester hydrochloride, and benzoylacetonitrile. In the presence of a catalytic amount of bifunctional chiral squaramide, the sequential one-pot annulation reaction provided a highly stereoselective way to construct fully substituted 2-pyrrolines containing two contiguous stereocenters, from imino esters with benzoylacetonitriles in good yields under mild conditions.

中文翻译：

2-吡咯啉的多组分合成和功能化的手性2-吡咯啉的有机催化不对称合成

通过进行简单且可商购的起始原料，即醛，甘氨酸酯盐酸盐和碳酸氢盐的多组分串联[2 + 2 +1]环化反应，已实现了功能化2-吡咯啉的绿色环保和原子经济的合成。苯甲酰基乙腈。在催化量的双官能手性方酰胺的存在下，连续的一锅法环合反应提供了高度立体选择性的方式，可以在温和的条件下，以高收率由亚氨基酯与苯甲酰基乙腈一起构建包含两个连续立体中心的完全取代的2-吡咯啉。

更新日期：2021-01-13

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