Diastereoselective synthesis of polycyclic indolines via dearomative [4 + 2] cycloaddition of 3-nitroindoles with ortho-aminophenyl p-quinone methides.
Org Biomol Chem
; 21(7): 1373-1378, 2023 Feb 15.
Article
em En
| MEDLINE
| ID: mdl-36723148
ABSTRACT
A formal [4 + 2] cycloaddition of 3-nitroindoles with ortho-aminophenyl p-quinone methides via a dearomatization process was developed. This method provides a facile approach for preparing tetrahydro-5H-indolo[2,3-b]quinolones with good results. With the bifunctional Cinchona alkaloid-squaramide as the catalyst, the asymmetric version of the reaction successfully afforded the corresponding chiral products with moderate to good enantioselectivities. This work represents the first dearomative cycloaddition of electron-deficient heteroarenes triggered by aza-Michael addition from p-QMs.
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MEDLINE
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En
Ano de publicação:
2023
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Article