Concise Preparation of Optically Active Heteroaryl α-(Hydroxyamino) Esters

A practical sequence for the synthesis of optically active heteroaryl α‐(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 substr...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-06, Vol.2014 (18), p.3773-3776
Main Authors: Murat-Onana, Marie Laure, Berini, Christophe, Denis, Jean-Noël, Poisson, Jean-François, Minassian, Frédéric, Pelloux-Léon, Nadia
Format: Article
Language:English
Subjects:
Chemical Sciences
Diastereoselectivity
Heterocycles
Hydroxyamino esters
Nitrones
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Summary:A practical sequence for the synthesis of optically active heteroaryl α‐(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 α‐(hydroxyamino) esters in good overall yields (36–62 %) with good enantiomeric excess values (76 to ≥98 %). The highly diastereoselective addition of heteroaromatics to a cyclic chiral nitrone allows access to a series of heteroaryl hydroxylamines. The scope of this reaction is presented on substrates possessing a pyrrole, an indole, or a furan core. The three‐step sequence affords α‐(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