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Concise Preparation of Optically Active Heteroaryl α‐(Hydroxyamino) Esters
Author(s) -
MuratOnana Marie Laure,
Berini Christophe,
Denis JeanNoël,
Poisson JeanFrançois,
Minassian Frédéric,
PellouxLéon Nadia
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402322
Subject(s) - chemistry , enantiomer , optically active , pyrrole , nitrone , combinatorial chemistry , furan , indole test , sequence (biology) , enantiomeric excess , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , cycloaddition , biochemistry
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 %).
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