The application of “backdoor induction” in bioinspired asymmetric catalysis?

RSC Advances Pub Date: 2012-04-13 DOI: 10.1039/C2RA20598J

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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