Concise Preparation of Optically Active Heteroaryl [alpha]-(Hydroxyamino) Esters

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...

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Veröffentlicht in:European journal of organic chemistry 2014-06, Vol.2014 (18), p.3773
Hauptverfasser: Murat-Onana, Marie Laure, Berini, Christophe, Denis, Jean-Noël, Poisson, Jean-François, Minassian, Frédéric, Pelloux-Leon, Nadia
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container_issue 18
container_start_page 3773
container_title European journal of organic chemistry
container_volume 2014
creator Murat-Onana, Marie Laure
Berini, Christophe
Denis, Jean-Noël
Poisson, Jean-François
Minassian, Frédéric
Pelloux-Leon, Nadia
description 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%).
doi_str_mv 10.1002/ejoc.201402322
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title Concise Preparation of Optically Active Heteroaryl [alpha]-(Hydroxyamino) Esters
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