Premium
The Construction of Quaternary Stereocenters by the Henry Reaction: Circumventing the Usual Reactivity of Substituted Glyoxals
Author(s) -
Blay Gonzalo,
HernándezOlmos Víctor,
Pedro José R.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002888
Subject(s) - nitromethane , stereocenter , reactivity (psychology) , enantioselective synthesis , ketone , chemistry , nitroaldol reaction , alkyl , enantiomer , organic chemistry , catalysis , medicine , alternative medicine , pathology
The enantioselective Henry reaction between alkyl‐ and arylglyoxal hydrates and nitromethane catalyzed by Cu II –iminopyridine complexes takes place regioselectively on the ketone carbonyl group to give chiral tertiary nitroaldols with high functional group density and enantiomeric excesses of up to 96 %. Both aromatic and aliphatic glyoxals are suitable substrates for this reaction.