proline-catalysed amination reactions in cyclic carbonate solventsproline-catalysed氨基化反应环碳酸酯溶剂.pdfVIP

Molecules 2011, 16, 3420-3432; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Proline-Catalysed Amination Reactions in Cyclic Carbonate Solvents Christopher Beattie, Michael North * and Pedro Villuendas School of Chemistry, Research Centre in Catalysis and Intensified Processing, Bedson Building, University of Newcastle, Newcastle upon Tyne, NE1 7RU, UK * Author to whom correspondence should be addressed; E-Mail: Michael.north@ncl.ac.uk; Tel.: +44-191-222-7128; Fax: +44-191-222-6929. Received: 6 April 2011; in revised form: 19 April 2011 / Accepted: 20 April 2011 / Published: 21 April 2011 Abstract: Propylene carbonate is shown to be an environmentally friendly and sustainable replacement for dichloromethane and acetonitrile in proline-catalysed α-hydrazinations of aldehydes and ketones. Enantioselectivities comparable to those obtained in conventional solvents or ionic liquids can be obtained, even when using a lower catalyst loading. Keywords: proline; amination; cyclic-carbonate 1. Introduction Proline (1) is unique amongst the proteinogenic amino acids in that it is a secondary amine. This leads to it having a special role in peptides and proteins as it cannot act as a hydrogen-bond donor, but is often found in β-turns [1-3]. Proline and its derivatives have also found many applications in synthetic chemistry as chiral-auxiliaries [4], chiral reagents [5,6] and most recently as chiral catalysts [7-12] where it was developments in proline-catalysed enamine c