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

Abstract

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.