Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

[Display omitted] We report the aldol addition of acetone to aromatic aldehydes in the presence of a large amount of water where the stereochemical outcome of the reactions can be tuned with achiral salt additives using a single proline-derived catalyst. Depending on the nature of the added salt the...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 52; pp. 7201 - 7205
Main Authors Gurka, András A., Szőri, Kornél, Szőllősi, György, Bartók, Mihály, London, Gábor
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.12.2015
Elsevier
Subjects
Aldol reaction
Chemistry
Chemistry, Organic
Dual stereocontrol
Emulsion
Enantioselective
Physical Sciences
Science & Technology
Water
Water
Aldol reaction
Enantioselective
Emulsion
Dual stereocontrol
KETONES
ENANTIOSELECTIVITY
ORGANOCATALYST
DIHYDROXYACETONE
ASYMMETRIC ALDOL
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Summary:[Display omitted] We report the aldol addition of acetone to aromatic aldehydes in the presence of a large amount of water where the stereochemical outcome of the reactions can be tuned with achiral salt additives using a single proline-derived catalyst. Depending on the nature of the added salt the (R) and (S) enriched products could be obtained. In the reaction of 2-nitrobenzaldehyde with acetone, NaOAc promoted the formation of the (S)-enantiomer (20% ee) while using NH4Cl the (R)-enantiomer was obtained in excess (58% ee). A similar inversion was observed for several other aromatic aldehydes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.11.051