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Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Amy McRae, Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

Oxazoline-substituted prolinamides catalyse the direct asymmetric aldol reaction between cyclohexanone and a range of aldehydes to give excellent conversions and enantioselectivities up to 84 % under optimum conditions. Reactions were highly substrate-specific with electron-deficient aldehydes giving the highest yields and ee values. The absolute configuration of the 4-chlorobenzaldehyde-derived product was unequivocally established as (2S,1'R) by single-crystal X-ray analysis, and the stereochemistry of the product was shown to be determined principally by the stereo chemistry of the proline fragment. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).


Publication metadata

Author(s): Doherty S, Knight JG, Mcrae A, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2008

Issue: 10

Pages: 1759-1766

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/ejoc.200700922

DOI: 10.1002/ejoc.200700922


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