Direct asymmetric aldol reactions in water catalysed by a highly active C2-Symmetrical bisprolinamide organocatalyst

Delaney, Joshua P. and Henderson, Luke C. 2012, Direct asymmetric aldol reactions in water catalysed by a highly active C2-Symmetrical bisprolinamide organocatalyst, Advanced synthesis and catalysis, vol. 354, no. 1, pp. 197-204.

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Title Direct asymmetric aldol reactions in water catalysed by a highly active C2-Symmetrical bisprolinamide organocatalyst
Author(s) Delaney, Joshua P.
Henderson, Luke C.
Journal name Advanced synthesis and catalysis
Volume number 354
Issue number 1
Start page 197
End page 204
Total pages 8
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Place of publication Weinheim, Germany
Publication date 2012-01
ISSN 1615-4150
1615-4169
Keyword(s) aldol reaction
organocatalysts
prolin-amides
pralines
water
Summary A novel C2-symmetrical bisprolinamide organocatalyst was synthesised and used to facilitate asymmetric direct aldol reactions in a water emulsion. Reactions were performed at room temperature with very low catalyst loadings (12.5 mol%) without the required use of additives, co-catalysts or extended reaction times (24 h). This catalyst system was then used with a variety of aldehyde substrates showing good reaction generality for benzaldehydes with cyclohexanone (dr range 77/23 to >99/1, anti/syn; ee range 33% to >99%) and moderate scope with cyclopentanone (dr range 45/55 to 76/24, anti/syn; ee range 14% to 68%). Ultra-low catalysts loadings (0.1 and 0.05 mol%) were also investigated demonstrating catalyst turnover numbers in the order of 1000.
Language eng
Field of Research 030503 Organic Chemical Synthesis
030601 Catalysis and Mechanisms of Reactions
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2012, Wiley-VCH Verlag GmbH&Co. KGaA
Persistent URL http://hdl.handle.net/10536/DRO/DU:30047042

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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