Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones: The Search for More Sustainable Selective and Practical Stoichiometric Oxidants
Anno: 2017
Autori: Matassini C., Cardona F.
Affiliazione autori: Univ Florence, Dipartimento Chim, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy; CNR INO, Via N Carrara 1, Sesto Fiorentino, FI, Italy.
Abstract: Nitrones are key intermediates for the total synthesis of nitrogen-containing natural products and analogues. The direct oxidation of the corresponding N,N-disubstituted hydroxylamines is one of the most straightforward methods to access such compounds. In this account, we describe the state of the art of this oxidative transformation using stoichiometric reagents. We will focus on the efforts made in the last 25 years to oxidize polyhydroxylated cyclic hydroxylamines, due to our long-standing interest in the total synthesis of alkaloids and other glycomimetics. Particular attention will be devoted to the discussion of the regioselectivity issue arising when unsymmetrical and highly functionalized substrates are involved
Giornale/Rivista: CHIMIA
Volume: 71 (9) Da Pagina: 558 A: 561
Maggiori informazioni: We thank Fondazione Donegani/Accademia dei Lincei for a fellowship to C.M.Parole chiavi: N,N-Disubstituted hydroxylamines; Nitrones; Oxidation; Regioselectivity; Stoichiometric reagentsDOI: 10.2533/chimia.2017.558Citazioni: 12dati da “WEB OF SCIENCE” (of Thomson Reuters) aggiornati al: 2025-02-09Riferimenti tratti da Isi Web of Knowledge: (solo abbonati) Link per visualizzare la scheda su IsiWeb: Clicca quiLink per visualizzare la citazioni su IsiWeb: Clicca qui