"Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives"
Youhei Takeda*, Yuki Ikeda, Akinobu Kuroda, Shino Tanaka, and Satoshi Minakata*
J. Am. Chem. Soc. 2014, 136, 8544–8547. DOI: 10.1021/ja5039616
* Highlighted in Org. Process Res. Dev. as "Some Items of Interest to Process R&D Chemists and Engineers"! !(link)
Abstract: A palladium-catalyzed stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines with arylboronic acids under mild conditions to construct a tertiary stereogenic center has been developed. N-heterocyclic carbene (NHC) ligands drastically promote the coupling, suppressing β-hydride elimination. The enantiospecific cross-coupling allowed us for preparation of a series of biologically important 2-arylphenethylamine derivatives in an enantiopure form.
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