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Carbene-Catalyzed Chemo-Selective Reactions of Enals and Aminobenzaldehydes for Access to Chiral Dihydroquinolines.

08:00 EDT 11th October 2019 | BioPortfolio

Summary of "Carbene-Catalyzed Chemo-Selective Reactions of Enals and Aminobenzaldehydes for Access to Chiral Dihydroquinolines."

A carbene-catalyzed reaction between α-bromoenals and 2-aminoaldehydes is developed. Key steps include chemo-selective reaction of the carbene catalyst with one of the aldehyde substrates (the bromoenal) to eventually generate 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 lead to chiral dihydroquinolines with high optical purities. The dihydroquinoline products, quickly prepared via our methods, can be readily transformed to a diverse set of functional molecules such as pyridines and chiral piperidines.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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