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Synthesis 2020; 52(18): 2650-2661
DOI: 10.1055/s-0040-1707176
DOI: 10.1055/s-0040-1707176
feature
Lewis Basic Amine Catalyzed Aza-Michael Reaction of Indole- and Pyrrole-3-carbaldehydes
We are grateful for the financial support from the National Natural Science Foundation of China (NSFC; 21961132004), the Higher Education Discipline Innovation Project (111 project; B18035), and the National Science Center (UMO-2018/30/Q/ST5/00466, Sheng programme).Further Information
Publication History
Received: 01 May 2020
Accepted after revision: 03 June 2020
Publication Date:
14 July 2020 (online)
Abstract
3-Formyl substituted indoles or pyrroles can form HOMO-raised dearomative aza-dienamine-type intermediates with secondary amines, which can undergo direct aza-Michael addition to β-trifluoromethyl enones to afford N-alkylated products efficiently, albeit with low to fair enantioselectivity. In addition, similar asymmetric aza-Michael additions of these heteroarenes and crotonaldehyde are realized under dual catalysis of chiral amines, and the adducts are obtained with moderate to good enantioselectivity.
Key words
aza-Michael addition - aminocatalysis - dearomative transformations - aza-dienamine - dual catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707176.
- Supporting Information
- CIF File
-
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