Format

Send to

Choose Destination
See comment in PubMed Commons below
Org Biomol Chem. 2013 May 7;11(17):2780-6. doi: 10.1039/c3ob27479a. Epub 2013 Mar 14.

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

Author information

1
Department of Biotechnology and Life Science, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, Japan. sohtome@riken.jp

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.

PMID:
23493979
DOI:
10.1039/c3ob27479a
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Royal Society of Chemistry
    Loading ...
    Support Center