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. Attached Files Name Description MIMEType Size Downloads Title Direct asymmetric aldol reactions in water catalysed by a highly active C2-Symmetrical bisprolinamide organocatalyst Author(s) Delaney, Joshua P. Henderson, Luke C. orcid.org/0000-0002-4244-2056 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 Collections: Faculty of Science, Engineering and Built Environment School of Life and Environmental Sciences Related Links Link Description Connect to published version (restricted access) Go to link with your DU access privileges     Unless expressly stated otherwise, the copyright for items in DRO is owned by the author, with all rights reserved. Versions Version Filter Type Mon, 13 Aug 2012, 13:09:34 EST Wed, 29 Aug 2012, 15:11:50 EST Wed, 29 Aug 2012, 15:13:04 EST Mon, 17 Jun 2013, 17:48:42 EST Thu, 15 May 2014, 10:09:38 EST Thu, 15 May 2014, 11:16:55 EST Fri, 06 Feb 2015, 10:59:33 EST Filtered Full Citation counts:   Cited 29 times in TR Web of Science Cited 29 times in Scopus Search Google Scholar Access Statistics: 720 Abstract Views, 3 File Downloads  -  Detailed Statistics Created: Mon, 13 Aug 2012, 13:09:34 EST