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DOI: 10.1055/s-0036-1588107
Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
Publication History
Received: 03 October 2016
Accepted after revision: 02 November 2016
Publication Date:
08 December 2016 (online)
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Abstract
A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared amines were screened as organocatalysts in the direct asymmetric aldol reaction between 4-nitrobenzaldehyde or isatin and acetone or cyclohexanone. The aldol adducts were obtained in good chemical yields, diastereoselectivity up to 97:3 (reactions with cyclohexanone), and enantioselectivity up to 71% ee. Trifluoroacetic acid and benzoic acid proved to be the best cocatalysts for the aldol process on 4-nitrobenzaldehyde and isatin, respectively.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588107.
- Supporting Information
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For selected recent applications of chiral imidazole derivatives in asymmetric catalysis, see:
For selected reviews covering primary amine catalysts, see: