Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel-Crafts Conjugate Addition of Indolizines.
Org Lett
; 23(24): 9548-9553, 2021 Dec 17.
Article
em En
| MEDLINE
| ID: mdl-34855406
ABSTRACT
An organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62-91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp2 C-H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
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Bases de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2021
Tipo de documento:
Article