Hyun-Suk Yeom
Department of Chemistry, Hanyang University, Seoul 133-791 Korea

Abstract:

Recently, we have been interested in transition metal catalyzed redox reaction because of their easy handling, safety of operation, and versatile reactivity. Also, we reported O-transfer protocols where reactive intermediates such as carbenoid, imine and azomethineylide substrates by Au-catalyzed redox reaction. This O-atom transfer protocols are efficient methods for increasingmolecular complexity of simple organic substrates, and thusreceived intense attention from a viewpoint of atom- and redox-economy.

We projected that the addition of hydroxyl amineinstead of nitrone and oxime as source of oxygen alkyne will lead to alpha-amino carbonyl compounds that constitute a fundamental organic building block. We realized this concept in an intramolecular fashion using alkyne tethered N-sulfonylhydroxylamines.The N-sulfonyl hydroxylamine derivatives as a precursor of 3-pyrrolidinones based on the hypothesis that the N-O cleavage will determine the overall rate and that the electron-withdrawing group on N-atom will facilitate the N-O cleavage.But depending on the alkynyl substituents, the reaction follows two distinct manifold, the other one was cyclic nitrones via sulfonyl migration.The details of this chemistry will be presented.