Department of Biotechnology and Life Science, Faculty of Technology, Tokyo University of Agriculture and Technology, 2-24-26 Naka-cho, Koganei, Japan
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Org. Biomol. Chem., 2013,11, 2780-2786
21 Dec 2012,
26 Feb 2013
First published online
27 Feb 2013
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.
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Organic & Biomolecular Chemistry
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