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Synthesis of N‑Oxyureas by Substitution and Cope-Type Hydroamination Reactions Using O‑Isocyanate Precursors

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journal contribution
posted on 22.11.2017, 18:30 authored by Meredith A. Allen, Ryan A. Ivanovich, Dilan E. Polat, André M. Beauchemin
Oxy-carbamate O-isocyanate precursors facilitate access to synthetically valuable N-oxyureas via substitution with amines. This work exploits the reactivity of suitable O-isocyanate precursors, identified by a thorough study highlighting the different reactivity of isocyanate masking groups. This led to bench-stable O-isocyanate precursors, offering improved versatility in the synthesis of N-oxyureas, and demonstrates the controlled reactivity of masked O-isocyanates. Suitable precursors also enabled the first example of Cope-type hydroamination of unsaturated hydroxyureas.