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Cyclic carbonates as sustainable solvents for proline-catalysed aldol reactions

Lookup NU author(s): Emeritus Professor Bill Clegg, Dr Ross Harrington, Professor Michael North, Francesca Pizzato, Dr Pedro Villuendas

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Abstract

Ethylene and propylene carbonates, which can be prepared from epoxides and carbon dioxide, are effective solvents for the proline-catalysed, 100% atom economical, asymmetric aldol reaction between enolisable and non-enolisable carbonyl compounds. The optimal cyclic carbonate to use for a particular aldol reaction along with the need for water as a cosolvent appear to be determined by the polarities of the various components present in the reaction mixture. Both cyclic and acyclic ketones can be used as the enamine precursor and react best with electron-deficient aldehydes, such as 4-nitrobenzaldehyde and pentafluorobenzaldehyde. Chemical yields of up to 99%, diastereoselectivities of up to 100% and enantioselectivities of up to 99% can be obtained. The relative and/or absolute configuration of three of the aldol products are determined unambiguously by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.


Publication metadata

Author(s): Clegg W, Harrington RW, North M, Pizzato F, Villuendas P

Publication type: Article

Publication status: Published

Journal: Tetrahedron: Asymmetry

Year: 2010

Volume: 21

Issue: 9-10

Pages: 1262-1271

Print publication date: 01/05/2010

ISSN (print): 0957-4166

ISSN (electronic): 1362-511X

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tetasy.2010.03.051

DOI: 10.1016/j.tetasy.2010.03.051


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