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Designing a Planar Chiral Rhodium Indenyl Catalyst for Regio- and Enantioselective Allylic C-H Amidation

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Title
Designing a Planar Chiral Rhodium Indenyl Catalyst for Regio- and Enantioselective Allylic C-H Amidation
Author(s)
Caitlin M. B. Farr; Amaan M. Kazerouni; Bohyun Park; Christopher D. Poff; Joonghee Won; Kimberly R. Sharp; Mu-Hyun Baik; Simon B. Blakey
Subject
SLIP-FOLD DISTORTION, ; BOND FUNCTIONALIZATION, ; SUBSTITUTION-REACTIONS, ; ASYMMETRIC CATALYSIS, ; 2+2+2 CYCLOADDITION, ; TRANSITION-METALS, ; LIGANDS, ; COMPLEXES, ; AMINATION, ; ACTIVATION
Publication Date
2020-08
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.32, pp.13996 - 14004
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society Chiral variants of group IX Cp and Cp* catalysts are well established and catalyze a broad range of reactions with high levels of enantioselectivity. Enantiocontrol in these systems results from ligand design that focuses on appropriate steric blocking. Herein we report the development of a new planar chiral indenyl rhodium complex for enantioselective C-H functionalization catalysis. The ligand design is based on establishing electronic asymmetry in the catalyst, to control enantioselectivity during the reactions. The complex is easily synthesized from commercially available starting materials and is capable of catalyzing the asymmetric allylic C-H amidation of unactivated olefins, delivering a wide range of high-value enantioenriched allylic amide products in good yields with excellent regio- and enantioselectivity. Computational studies suggest that C-H cleavage is rate- and enantio-determining, while reductive C-N coupling from the Rh-v-nitrenoid intermediate is regio-determining
URI
https://pr.ibs.re.kr/handle/8788114/7684
DOI
10.1021/jacs.0c07305
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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