Diastereoselective Synthesis of N-Methylspiroindolines by Intramolecular Mizoroki-Heck Annulations.
ACS Omega
; 7(36): 32525-32535, 2022 Sep 13.
Article
em En
| MEDLINE
| ID: mdl-36120037
ABSTRACT
Spiroindolines represent a privileged structure in medicinal chemistry, although stereocontrol around the spirocarbon can be a synthetic challenge. Here we present a palladium(0)-catalyzed intramolecular Mizoroki-Heck annulation reaction from (+)-Vince lactam-derived cyclopentenyl-tethered 2-bromo-N-methylanilines for the formation of N-methylspiroindolines. A series of 14 N-methylspiroindolines were synthesized in 59-81% yield with diastereoselectivity >98%, which was rationalized by density functional theory calculations and confirmed through X-ray crystallography. One spiroindoline was converted to an N- and C-terminal protected rigidified unnatural amino acid, which could be orthogonally deprotected.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
ACS Omega
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Suécia