Pictet–Spengler reaction based on in situ generated α-amino iminium ions through the Heyns rearrangement,Organic Chemistry Frontiers

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Pictet–Spengler reaction based on in situ generated α-amino iminium ions through the Heyns rearrangement
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-09-18 , DOI: 10.1039/d0qo00722f
Jun-xiu Liang _{1,

2,

3,

4,

5} , Guo-bin Yang _{1,

2,

3,

4} , Yong-po Zhang _{1,

2,

3,

4} , Dong-dong Guo _{1,

2,

3,

4} , Jin-zhong Zhao _{1,

2,

3,

4} , Guang-xun Li _{4,

5,

6,

7,

8} , Zhuo Tang _{4,

5,

6,

7,

8}

Affiliation

A useful tandem reaction via the Heyns rearrangement and Pictet–Spengler reaction was developed which ensured the synthesis of complex N-heteropolycycles containing tetrahydro-β-carboline with high yield (up to 96%) and dr (99 : 1). The reaction proceeded smoothly with a catalytic Brønsted acid as a catalyst. The reaction mechanism was investigated which demonstrated that the tandem reaction proceeded due to the in situ produced α-amino iminium ions via the Heyns rearrangement.

中文翻译：

通过Heyns重排基于原位产生的α-氨基亚胺离子的Pictet-Spengler反应

通过Heyns重排和Pictet-Spengler反应开发了有用的串联反应，该反应可确保合成高产率（最高96％）和dr（99：1）的含有四氢-β-咔啉的复杂N-杂多环。用催化布朗斯台德酸作为催化剂使反应顺利进行。研究了反应机理，结果表明串联反应是由于通过Heyns重排原位产生的α-氨基亚胺离子而进行的。

更新日期：2020-10-13

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