Tandem Nucleophilic Addition−Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines

A highly stereoselective synthesis of fluorinated 1,3-disubstituted isoindolines is described. To this end, a tandem reaction consisting of a diastereoselective addition of fluorinated nucleophiles to Ellman’s N-(tert-butanesulfinyl)imines followed by an intramolecular aza-Michael reaction has been...

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Veröffentlicht in:	Organic letters 2010-12, Vol.12 (23), p.5494-5497
Hauptverfasser:	Fustero, Santos, Moscardó, Javier, Sánchez-Roselló, María, Rodríguez, Elsa, Barrio, Pablo
Format:	Artikel
Sprache:	eng
Schlagworte:	Aza Compounds - chemistry Halogenation Hydrolysis Indoles - chemical synthesis Isoindoles - chemical synthesis Models, Molecular Molecular Structure Stereoisomerism
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container_issue	23
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container_title	Organic letters
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creator	Fustero, Santos Moscardó, Javier Sánchez-Roselló, María Rodríguez, Elsa Barrio, Pablo
description	A highly stereoselective synthesis of fluorinated 1,3-disubstituted isoindolines is described. To this end, a tandem reaction consisting of a diastereoselective addition of fluorinated nucleophiles to Ellman’s N-(tert-butanesulfinyl)imines followed by an intramolecular aza-Michael reaction has been developed. This strategy allows for the construction of isoindolines bearing several degrees of fluorination (mono-, di-, or trifluoromethyl as well as heavier fluorinated groups). In the majority of all cases, the products are formed as single isomers.
doi_str_mv	10.1021/ol102341n
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subjects	Aza Compounds - chemistry Halogenation Hydrolysis Indoles - chemical synthesis Isoindoles - chemical synthesis Models, Molecular Molecular Structure Stereoisomerism
title	Tandem Nucleophilic Addition−Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines
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