Catalytic Asymmetric Synthesis of Dihydropyrido[1,2-a]indoles from Nitrones and Allenoates
Wiktoria H Pace1, Dong-Liang Mo1, Tyler W Reidl1
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL, 60607, USA.
Abstract:
An asymmetric method for the synthesis of dihydropyrido[1,2-a]indoles from mixtures of nitrones and allenoates has been developed. This transformation showcases the use of squaramide catalysis in a complicated cascade system that has been shown to be highly sensitive to reaction conditions and substituent effects. The new method provides access to enantiomerically enriched dihydropyridoindoles from modular, non-indole reagents. The optimization and scope of the new transformation is discussed in addition to initial mechanistic experiments that indicate the role of the catalyst.
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