One-Pot Synthesis of N-Hydroxypyrroles via Soft α-Vinyl Enolization of (E)-β-Chlorovinyl Ketones: A Traceless Arylsulfinate Mediator Strategy.

A traceless arylsulfinate mediator strategy has been developed to switch the reaction course of β-chlorovinyl ketones with N-hydroxyamine. The soft α-vinyl enolization of (E)-β-chlorovinyl ketones was conducted in the presence of sodium arylsulfinate to give transient alkenyl sulfones that in turn reacted with NH2OH to give novel access to N-hydroxypyrroles. The mechanistic studies revealed the initial formation of oxazine intermediates that rearranged to thermodynamically stable aromatic products, N-hydroxypyrroles, under microwave-assisted heating conditions.

Citation

Divya Bhatt, Soyeon Chae, Hun Young Kim, Kyungsoo Oh. One-Pot Synthesis of N-Hydroxypyrroles via Soft α-Vinyl Enolization of (E)-β-Chlorovinyl Ketones: A Traceless Arylsulfinate Mediator Strategy. Organic letters. 2022 Apr 15;24(14):2636-2640

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PMID: 35385289

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