Copper- and Chiral Nitroxide-Catalyzed Oxidative Kinetic Resolution of Axially Chiral N‑Arylpyrroles
Organic Letters(2022)
Abstract
A readily prepared C2-symmetric, α-hydrogen-substituted chiral hydroxylamine serves as a precatalyst to generate a chiral nitroxide in situ. This chiral nitroxide catalyst in combination with a copper co-catalyst functions as an oxidant for an unprecedented enantioselective oxidative kinetic resolution (OKR) of racemic axially chiral N-arylpyrrole alcohols using atmospheric oxygen as an environmentally friendly terminal oxidant. The OKR process provides the axially chiral N-arylpyrroles in er up to 3.5:96.5 and with s factors up to 24.
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Key words
axially chiral,kinetic resolution,nitroxide-catalyzed
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