Iridium(III)-Catalyzed Intermolecular C(sp³)-H Amidation for the Synthesis of Chiral 1,2-Diamines

Geraci, Andrea and Stojiljković, Uros and Antien, Kevin and Salameh, Nihad and Baudoin, Olivier. (2023) Iridium(III)-Catalyzed Intermolecular C(sp³)-H Amidation for the Synthesis of Chiral 1,2-Diamines. Angewandte Chemie International Edition, 62 (42). e202309263.

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Chiral 1,2-diamines are privileged scaffolds among bioactive natural products, active pharmaceutical ingredients, ligands for transition-metal-based asymmetric catalysis and organocatalysts. Despite this interest, the construction of chiral 1,2-diamine motifs still remains a challenge. To address this, an iridium(III)-catalyzed intermolecular C(sp3)-H amidation reaction was developed. This method relies on the design of a new, cheap and cleavable exo-protecting/directing group derived from camphorsulfonic acid, which is directly installed from easily accessible precursors, and furnishes scalemic free 1,2-diamines upon cleavage of both nitrogen substituents. It was found applicable to both α-secondary and α-tertiary-1,2-diamines, for which a two-step protocol involving intermolecular olefin hydroamination and C(sp3)-H amidation was developed. Kinetic and computational studies provided insights into the observed reactivity difference between pairs of diastereoisomeric substrates.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:18 Oct 2023 07:10
Deposited On:18 Oct 2023 07:10

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