l-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions

l-Proline-catalysed direct asymmetric aldol reaction of acetone with various aldehydes in PEG-400 is described. Recycling of the catalyst and solvent (PEG) was possible up to ten runs without loss of catalyst activity. l-Proline was also found to be an efficient catalyst for the asymmetric transfer...

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Bibliographic Details
Published inTetrahedron Vol. 62; no. 2; pp. 338 - 345
Main Authors Chandrasekhar, S., Reddy, N. Ramakrishna, Sultana, S. Shameem, Narsihmulu, Ch, Reddy, K. Venkatram
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.01.2006
Elsevier
Subjects
Aldol reaction
Chemistry
Chemistry, Organic
l-Proline
PEG-400
Physical Sciences
Science & Technology
Transfer aldol reaction
Aldol reaction
l-Proline
Transfer aldol reaction
PEG-400
aldol reaction
transfer aldol reaction
POLY(ETHYLENE GLYCOL) PEG
AQUEOUS-MEDIA
3-COMPONENT MANNICH REACTION
IONIC LIQUID
ALDEHYDES
EQUIVALENTS
ALLYL-TRANSFER REACTION
TRANSFER-TISCHTSCHENKO REACTION
L-proline
SMALL ORGANIC-MOLECULES
BETA-HYDROXY KETONES
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Summary:l-Proline-catalysed direct asymmetric aldol reaction of acetone with various aldehydes in PEG-400 is described. Recycling of the catalyst and solvent (PEG) was possible up to ten runs without loss of catalyst activity. l-Proline was also found to be an efficient catalyst for the asymmetric transfer aldol reaction between various aldehydes and diacetone alcohol for the first time. Good yields and enantioselectivities were observed with both methods. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.09.122