Atroposelective synthesis of <i>N</i>-aryl peptoid atropisomers <i>via</i> a palladium(<scp>ii</scp>)-catalyzed asymmetric C–H alkynylation strategy

Abstract

-aryl peptoid atropisomers in good yields with excellent enantioselectivities (up to 99% yield and 99% ee) by palladium-catalyzed asymmetric C-H alkynylation. The inexpensive and commercially available l-pyroglutamic acid was used as an efficient chiral ligand. The exceptional compatibility of the C-H alkynylation with various peptoid oligomers renders this procedure valuable for peptoid modifications. Computational studies suggested that the amino acid ligand distortion controls the enantioselectivity in the Pd/l-pGlu-catalyzed C-H bond activation step.

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