NHC‐Catalyzed Chemoselective Reactions of Enals and Aminobenzaldehydes for Access to Chiral Dihydroquinolines

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Abstract
An N‐heterocyclic carbene (NHC)‐catalyzed reaction between α‐bromoenals and 2‐aminoaldehydes has been developed. Key steps include chemoselective reaction of the NHC catalyst with one of the aldehyde substrates (the bromoenal) to eventually generate an α,β‐unsaturated acylazolium intermediate. Addition of the nitrogen atom of aminoaldehyde to the unsaturated azolium ester intermediate followed by intramolecular aldol reaction, β‐lactone formation, and decarboxylation leads to chiral dihydroquinolines with high optical purity. The dihydroquinoline products, which are quickly prepared by using this method, can be readily transformed into a diverse set of functional molecules such as pyridines and chiral piperidines.
Funding Information
  • National Natural Science Foundation of China (21772029, 21801051 and 21807019)
  • Guizhou Provincial Science and Technology Department ([2016]5649)
  • National Research Foundation Singapore (NRF-NRFI2016-06)
  • Nanyang Technological University

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