Anionic-Anionic Asymmetric Tandem Reactions: One-Pot Synthesis of Optically Pure Fluorinated Indolines from 2-p-Tolylsulfinyl Alkylbenzenes

Anionic-Anionic Asymmetric Tandem Reactions: One-Pot Synthesis of Optically Pure Fluorinated Indolines from 2-p-Tolylsulfinyl Alkylbenzenes

Chirality switch up: A novel strategy has been developed to give optically pure fluorinated indolines with one or two stereogenic centers (see scheme; AN=nucleophilic addition, PG=protecting group, SNAr=intramolecular nucleophilic aromatic substitution, Tol=tolyl). Almost complete stereoselectivity...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (41), p.7941-7944
Hauptverfasser: García Ruano, José Luis, Alemán, José, Catalán, Silvia, Marcos, Vanesa, Monteagudo, Silvia, Parra, Alejandro, del Pozo, Carlos, Fustero, Santos
Format: Artikel
Sprache:eng
Schlagworte:
Anions - chemistry
asymmetric synthesis
Benzene - chemistry
Fluorine - chemistry
Indoles - chemical synthesis
indolines
Stereoisomerism
γ-sulfinyl carbanions
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Chirality switch up: A novel strategy has been developed to give optically pure fluorinated indolines with one or two stereogenic centers (see scheme; AN=nucleophilic addition, PG=protecting group, SNAr=intramolecular nucleophilic aromatic substitution, Tol=tolyl). Almost complete stereoselectivity and mild reaction conditions are the key features of the title reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802885