Chiral N-hydroxybenzamides (1H–3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1•–3•. The latter species have been generated by oxidation of 1H–3H with Pb(OAc)4 or hydrogen abstraction from 1H–3H by the tert-butoxyl radical and characterized by UV–vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1•–3• from three chiral benzylic substrates (1-phenylethylamine, 1-phenylethanol, and α-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 ≤ kH(S)/kH(R) ≤ 2.

ChiralN-Hydroxybenzamides as Potential Catalysts for Aerobic Asymmetric Oxidations

FRANCHI, PAOLA;LUCARINI, MARCO
2014

Abstract

Chiral N-hydroxybenzamides (1H–3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1•–3•. The latter species have been generated by oxidation of 1H–3H with Pb(OAc)4 or hydrogen abstraction from 1H–3H by the tert-butoxyl radical and characterized by UV–vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1•–3• from three chiral benzylic substrates (1-phenylethylamine, 1-phenylethanol, and α-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 ≤ kH(S)/kH(R) ≤ 2.
Maria Grazia Capraro;Paola Franchi;Osvaldo Lanzalunga;Andrea Lapi;Marco Lucarini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/340516
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