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Issue 17, 2013
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Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst

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Abstract

Here we describe our studies on solvent-dependent enantiodivergent Mannich-type reactions utilizing conformationally flexible guanidine/bisthiourea organocatalyst (S,S)-1. Our mechanistic investigations revealed that the stereo-determining steps in both the (R)- and (S)-selective Mannich-type reactions are governed by the cooperative effect of guanidine and thiourea in the inherently monomeric structure of (S,S)-1. Based on the mechanistic similarity between the (R)- and (S)-selective Mannich-type reactions, we discovered that (S,S)-1-catalyzed reactions show unique reversibility in mixed solvent systems. We highlight the development of sequential enantiodivergent organocatalysis using (S,S)-1, which allows enantio-switching with single-flask operation and high in situ tunability.

Graphical abstract: Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst

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Publication details

The article was received on 21 Dec 2012, accepted on 26 Feb 2013 and first published on 27 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB27479A
Citation: Org. Biomol. Chem., 2013,11, 2780-2786
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    Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst

    Y. Sohtome, T. Yamaguchi, S. Tanaka and K. Nagasawa, Org. Biomol. Chem., 2013, 11, 2780
    DOI: 10.1039/C3OB27479A

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