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Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C–H Functionalisations

Title	Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C–H Functionalisations
Authors	Young Sebastian Ye, Aragorn Laverny, Matthew D. Wodrich, Ruben Laplaza, Farzaneh Fadaei-Tirani, Rosario Scopelliti, Clemence Corminboeuf, Nicolai Cramer
Magazine	Journal of the American Chemical Society
Date	12/06/2024
DOI	10.1021/jacs.4c13279
Introduction	Chiral cyclopentadienyl (Cp X) metal complexes are essential in asymmetric catalysis due to their high reactivity and selectivity. Planar-chiral rhodium and iridium cyclopentadienyl complexes stand out for their potential in catalyst design while maintaining structural simplicity. However, their usage is limited due to inefficient synthesis methods that rely on lengthy chiral auxiliary routes or HPLC resolution. To overcome this, a straightforward, highly enantiospecific synthesis has been developed, involving a point-to-planar chirality transfer complexation between a metal-carboxylate precursor and a chiral cyclopentadiene. This approach circumvents the typical racemate-producing stereoablative complexation. Using this method, a diverse library of planar chiral Cp-Rh(I), Cp-Ir(I), Cp-Rh(III), and Cp-Ir(III) complexes was created. The enantiospecific complexation can also be combined with Au-catalysed cyclisation in a one-pot process, involving complex chirality transfers. Computational predictions guided the tuning of a Cp X-Rh complex for optimised reactivity and selectivity in asymmetric C–H functionalisation of benzamide with challenging alkenes. An optimised Cp X-Rh complex demonstrated excellent catalytic performance and high selectivity for difficult alkene substrates that were previously problematic.
Quote	Young Sebastian Ye, Aragorn Laverny and Matthew D. Wodrich et al. Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C–H Functionalizations. J. Am. Chem. Soc. 2024. Vol. 146(50):34786-34795. DOI: 10.1021/jacs.4c13279
Element	Iridium (Ir) , Rhodium (Rh)
Materials	Chemical Compounds
Industry	Chemical & Pharmacy

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