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EnglishChiral 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.
| Titolo: | ChiralN-Hydroxybenzamides as Potential Catalysts for Aerobic Asymmetric Oxidations | |
| Autore/i: | Maria Grazia Capraro; FRANCHI, PAOLA; Osvaldo Lanzalunga; Andrea Lapi; LUCARINI, MARCO | |
| Autore/i Unibo: | ||
| Anno: | 2014 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/jo500844c | |
| 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. | |
| Data prodotto definitivo in UGOV: | 2014-09-15 17:00:15 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/340516
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