Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes.
J Am Chem Soc
; 144(3): 1087-1093, 2022 01 26.
Article
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| MEDLINE
| ID: mdl-35007081
ABSTRACT
Enantioselective [3 + 2] annulation of N-heteroarenes with alkynes has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand and reducing reagent. A variety of electron-deficient N-heteroarenes, including quinolines, isoquinolines, quinoxaline, and pyridines, and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope and good functionality tolerance. Annulation of electron-rich indoles with alkynes is also developed. This protocol provides a straightforward access to a variety of N-spiroheterocyclic molecules in excellent enantioselectivities (76 examples, up to 99% ee).
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2022
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Article