Silver-catalyzed enantioselective propargylic C–H bond amination through rational ligand design

M Ju, EE Zerull, JM Roberts, M Huang… - Journal of the …, 2020 - ACS Publications
Asymmetric C–H amination via nitrene transfer is a powerful tool to prepare enantioenriched
amine precursors from abundant C–H bonds. Herein, we report a regio-and enantioselective
synthesis of γ-alkynyl γ-aminoalcohols via a silver-catalyzed propargylic C–H amination.
The protocol was enabled by a new bis (oxazoline)(BOX) ligand designed via a rapid
structure–activity relationship (SAR) analysis. The method utilizes accessible carbamate
esters bearing γ-propargylic C–H bonds and furnishes versatile products in good yields and …

Silver-Catalyzed Enantioselective Propargylic C–H Bond Amination Through Rational Ligand Design

E Zerull, J Roberts, M Huang, J Schomaker - 2020 - chemrxiv.org
Asymmetric C–H amination via nitrene transfer (NT) is a powerful tool for the preparation of
enantioenriched amine building blocks from abundant C–H bonds. Herein, we report a
highly regio-and enantioselective synthesis of-alkynyl-amino alcohol motifs via a silver-
catalyzed propargylic C–H amination. The protocol was enabled by development of a new
bis (oxazoline)(BOX) ligand through a rapid structure-activity relationship (SAR) analysis.
The method utilizes readily accessible carbamate ester substrates bearing-propargylic C …
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