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

András A. Gurka, K. Szöri, G. Szöllősi, M. Bartók, Gábor London

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7201-7205
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number52
DOIs
Publication statusPublished - Dec 30 2015

Fingerprint

Stereochemistry
2-nitrobenzaldehyde
Enantiomers
Acetone
Aldehydes
Tuning
Salts
Catalysts
Water
Proline
3-hydroxybutanal

Keywords

  • Aldol reaction
  • Dual stereocontrol
  • Emulsion
  • Enantioselective
  • Water

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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abstract = "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.",
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T1 - Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

AU - Gurka, András A.

AU - Szöri, K.

AU - Szöllősi, G.

AU - Bartók, M.

AU - London, Gábor

PY - 2015/12/30

Y1 - 2015/12/30

N2 - 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.

AB - 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.

KW - Aldol reaction

KW - Dual stereocontrol

KW - Emulsion

KW - Enantioselective

KW - Water

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