Issue 20, 2020

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

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.

Graphical abstract: Pictet–Spengler reaction based on in situ generated α-amino iminium ions through the Heyns rearrangement

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jun 2020
Accepted
17 Sep 2020
First published
18 Sep 2020

Org. Chem. Front., 2020,7, 3242-3246

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

J. Liang, G. Yang, Y. Zhang, D. Guo, J. Zhao, G. Li and Z. Tang, Org. Chem. Front., 2020, 7, 3242 DOI: 10.1039/D0QO00722F

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