Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki–Miyaura Arylation of 2‑Arylaziridines: Synthesis of Enantioenriched 2‑Arylphenethylamine Derivatives

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 efficiently promote the coupling, suppressing β-hydr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-06, Vol.136 (24), p.8544-8547
Main Authors: Takeda, Youhei, Ikeda, Yuki, Kuroda, Akinobu, Tanaka, Shino, Minakata, Satoshi
Format: Article
Language:English
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Summary: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 efficiently 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5039616