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A highly enantioselective, moderately anti-selective aldol reaction using a novel hydrazone moiety as stereo director

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JournalTETRAHEDRON-ASYMMETRY
DatePublished - 14 Nov 2005
Issue number22
Volume16
Number of pages4
Pages (from-to)3615-3618
Original languageEnglish

Abstract

The use of novel hydrazones as stereo directors with a view to develop a highly enantioselective, an ti-di astereo select i ve aldol addition procedure has been investigated. A number of proline-derived hydrazones were produced and their effectiveness in directing simple alkylation of aza-enolates investigated. The most promising of these hydrazones were then used in the aldol reaction. The substituent on the oxygen of the proline had a profound effect on both the magnitude and the sense of asymmetric induction. The optimum hydrazone for the formal aldol reaction between pentanone and propionaldehyde gave a diastereoselectivity of 37% in favour of the anti-isomer while both isomers had an ee of 83-84%. (c) 2005 Elsevier Ltd. All rights reserved.

    Research areas

  • METALATED CHIRAL HYDRAZONES, ASYMMETRIC-SYNTHESIS, N-DIMETHYLHYDRAZONES, ALKYLATION, ALDEHYDES, KETONES, NITROSATION, EFFICIENT, ADDITIONS, IMINES

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