Pictet–Spengler reaction based on in situ generated α-amino iminium ions through the Heyns rearrangement
Literature Information
Publication Date
2020-09-18
DOI
10.1039/D0QO00722F
Impact Factor
5.281
Authors
Guo-bin Yang, Yong-po Zhang, Dong-dong Guo, Jin-zhong Zhao, Guang-xun Li, Zhuo Tang
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide
CAS Number:
1352810-38-8
Molecular Formula:
C53H39O4P
![Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate structure](https://static.chemtradehub.com/structs/313/313490-90-3-dd15.webp "Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate structure")
Ethyl ({[(2-methyl-2-propanyl)oxy]carbonyl}amino)(2-pyridinyl)acetate
CAS Number:
313490-90-3
Molecular Formula:
C14H20N2O4
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