Concise Preparation of Optically Active Heteroaryl [alpha]-(Hydroxyamino) Esters
A practical sequence for the synthesis of optically active heteroaryl [alpha]-(hydroxyamino) esters was explored. The highly diastereoselective addition of heteroaromatics to a cyclic chiral nitrone allowed access to a series of heteroaryl hydroxylamines. The scope of this reaction was evaluated on...
Gespeichert in:
Veröffentlicht in: | European journal of organic chemistry 2014-06, Vol.2014 (18), p.3773 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | A practical sequence for the synthesis of optically active heteroaryl [alpha]-(hydroxyamino) esters was explored. The highly diastereoselective addition of heteroaromatics to a cyclic chiral nitrone allowed access to a series of heteroaryl hydroxylamines. The scope of this reaction was evaluated on substrates possessing a pyrrole, an indole, or a furan core. The three-step sequence afforded the [alpha]-(hydroxyamino) esters in good overall yields (36-62%) with good enantiomeric excess values (76 to ≥98%). |
---|---|
ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201402322 |