New simple hydrophobic proline derivatives as highly active and stereoselective catalysts for the direct asymmetric aldol reaction in aqueous medium

Giacalone F; Gruttadauria M; Lo Meo P; Riela S; Noto R

Risultato della ricerca: Article

92 Citazioni (Scopus)

Abstract

New 4-substituted acyloxyproline derivatives with different hydrophobic properties of the acyl group were easily synthesized and used as catalysts in the direct asymmetric aldol reaction between cyclic ketones (cyclohexanone and cyclopentanone) and several substituted benzaldehydes. Reactions were carried out using water, this being the best reaction medium examined. Screening of these catalysts showed that compounds bearing the most hydrophobic acyl chains [4-phenylbutanoate and 4-(pyren-1-yl)butanoate] provided better results. The latter catalysts were successfully used in only 2 mol% at room temperature without additives to give aldol products in excellent stereoselectivities. These results demonstrate that derivatization of the proline moiety with the proper simple hydrophobic substituent in the 4-position can furnish highly active and stereoselective catalysts without the need of additional chiral backbones in the molecule. Finally, an explanation of the observed stereoselectivities in the presence of water is provided.
Lingua originaleEnglish
pagine (da-a)2747-2760
Numero di pagine14
RivistaADVANCED SYNTHESIS & CATALYSIS
Volume350
Stato di pubblicazionePublished - 2008

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Proline
Derivatives
Stereoselectivity
Catalysts
Bearings (structural)
Benzaldehydes
Water
Ketones
Screening
Molecules
3-hydroxybutanal
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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New simple hydrophobic proline derivatives as highly active and stereoselective catalysts for the direct asymmetric aldol reaction in aqueous medium. / Giacalone F; Gruttadauria M; Lo Meo P; Riela S; Noto R.

In: ADVANCED SYNTHESIS & CATALYSIS, Vol. 350, 2008, pag. 2747-2760.

Risultato della ricerca: Article

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abstract = "New 4-substituted acyloxyproline derivatives with different hydrophobic properties of the acyl group were easily synthesized and used as catalysts in the direct asymmetric aldol reaction between cyclic ketones (cyclohexanone and cyclopentanone) and several substituted benzaldehydes. Reactions were carried out using water, this being the best reaction medium examined. Screening of these catalysts showed that compounds bearing the most hydrophobic acyl chains [4-phenylbutanoate and 4-(pyren-1-yl)butanoate] provided better results. The latter catalysts were successfully used in only 2 mol{\%} at room temperature without additives to give aldol products in excellent stereoselectivities. These results demonstrate that derivatization of the proline moiety with the proper simple hydrophobic substituent in the 4-position can furnish highly active and stereoselective catalysts without the need of additional chiral backbones in the molecule. Finally, an explanation of the observed stereoselectivities in the presence of water is provided.",
author = "{Giacalone F; Gruttadauria M; Lo Meo P; Riela S; Noto R} and Renato Noto and Michelangelo Gruttadauria and {Lo Meo}, {Paolo Maria Giuseppe} and Serena Riela and Francesco Giacalone",
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T1 - New simple hydrophobic proline derivatives as highly active and stereoselective catalysts for the direct asymmetric aldol reaction in aqueous medium

AU - Giacalone F; Gruttadauria M; Lo Meo P; Riela S; Noto R

AU - Noto, Renato

AU - Gruttadauria, Michelangelo

AU - Lo Meo, Paolo Maria Giuseppe

AU - Riela, Serena

AU - Giacalone, Francesco

PY - 2008

Y1 - 2008

N2 - New 4-substituted acyloxyproline derivatives with different hydrophobic properties of the acyl group were easily synthesized and used as catalysts in the direct asymmetric aldol reaction between cyclic ketones (cyclohexanone and cyclopentanone) and several substituted benzaldehydes. Reactions were carried out using water, this being the best reaction medium examined. Screening of these catalysts showed that compounds bearing the most hydrophobic acyl chains [4-phenylbutanoate and 4-(pyren-1-yl)butanoate] provided better results. The latter catalysts were successfully used in only 2 mol% at room temperature without additives to give aldol products in excellent stereoselectivities. These results demonstrate that derivatization of the proline moiety with the proper simple hydrophobic substituent in the 4-position can furnish highly active and stereoselective catalysts without the need of additional chiral backbones in the molecule. Finally, an explanation of the observed stereoselectivities in the presence of water is provided.

AB - New 4-substituted acyloxyproline derivatives with different hydrophobic properties of the acyl group were easily synthesized and used as catalysts in the direct asymmetric aldol reaction between cyclic ketones (cyclohexanone and cyclopentanone) and several substituted benzaldehydes. Reactions were carried out using water, this being the best reaction medium examined. Screening of these catalysts showed that compounds bearing the most hydrophobic acyl chains [4-phenylbutanoate and 4-(pyren-1-yl)butanoate] provided better results. The latter catalysts were successfully used in only 2 mol% at room temperature without additives to give aldol products in excellent stereoselectivities. These results demonstrate that derivatization of the proline moiety with the proper simple hydrophobic substituent in the 4-position can furnish highly active and stereoselective catalysts without the need of additional chiral backbones in the molecule. Finally, an explanation of the observed stereoselectivities in the presence of water is provided.

UR - http://hdl.handle.net/10447/28780

M3 - Article

VL - 350

SP - 2747

EP - 2760

JO - Journal fur Praktische Chemie

JF - Journal fur Praktische Chemie

SN - 0941-1216

ER -