Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 18, Pages 2650-2661Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707176
Keywords
aza-Michael addition; aminocatalysis; dearomative transformations; aza-dienamine; dual catalysis
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Funding
- National Natural Science Foundation of China (NSFC) [21961132004]
- Higher Education Discipline Innovation Project (111 project) [B18035]
- National Science Center [UMO-2018/30/Q/ST5/00466]
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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 beta-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.
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