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- Title
NHC‐Catalyzed Chemoselective Reactions of Enals and Aminobenzaldehydes for Access to Chiral Dihydroquinolines.
- Authors
Wu, Shuquan; Liu, Changyi; Luo, Guoyong; Jin, Zhichao; Zheng, Pengcheng; Chi, Yonggui Robin
- 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.
- Subjects
CHEMOSELECTIVITY; DECARBOXYLATION; ENANTIOMERIC purity; ALDOLS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 51, p18581
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201909479