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Issue 13, 2012
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The application of “backdoor induction” in bioinspired asymmetric catalysis

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Abstract

Amino acid substituted monodentate triphenylphosphine ligands Lig-Aa1-Aa2-Aa3-Z 5 and 6, with a C-terminal ester or amide group, respectively, were prepared in a few simple synthetic steps. Supramolecular in situ formed complexes [Rh(COD)(Lig-Aa1-Aa2-Aa3-Z)2]BF43 and 4 with a prochiral coordination sphere of the metal are selective hydrogenation catalysts (up to 68% ee). The selectivity is induced by transmission of chirality via distant hydrogen-bonded amino acids with a Herrick-like secondary structure (“backdoor induction”).

Graphical abstract: The application of “backdoor induction” in bioinspired asymmetric catalysis

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Publication details

The article was received on 02 Apr 2012, accepted on 10 Apr 2012 and first published on 13 Apr 2012


Article type: Paper
DOI: 10.1039/C2RA20598J
Citation: RSC Adv., 2012,2, 5729-5737
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    The application of “backdoor induction” in bioinspired asymmetric catalysis

    Z. Kokan and S. I. Kirin, RSC Adv., 2012, 2, 5729
    DOI: 10.1039/C2RA20598J

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