RT Journal Article
T1 Two-carbon ring expansion of bicyclic aziridines to oxazocines via aryne insertion into a s C–N bond
A1 Rampon, D. S.
A1 Trinh, T. A.
A1 Pan, Y.
A1 Thein, S.
A1 Kailing, J. W.
A1 Guzei, I. A.
A1 Fernández López, Israel
A1 Schomaker, J. M.
AB Oxazocines are medium-sized N,O-heterocycles that are motifs in reported bioactive compounds; thus, methods for their rapid preparation and functionalization are of significant interest, particularly to increase their representation in current drug libraries. In this work, a mild method to access oxazocines through aryne insertion into the σ C–N bond of carbamate-tethered bicyclic aziridines is described. This work unlocks a complementary reactivity mode for bicyclic aziridines via a two-carbon ring expansion, which preserves both the strained ring and its stereochemical information for further modifications. Mechanistic studies of the reaction pathway using Density Functional Theory computations indicate that oxazocine formation via nucleophilic acyl substitution of the carbonyl group of the carbamate is kinetically preferred over alternative products arising from aziridine ring-opening pathways.
PB RSC
YR 2025
FD 2025-09-16
LK https://hdl.handle.net/20.500.14352/131906
UL https://hdl.handle.net/20.500.14352/131906
LA eng
NO Rampon, Daniel S., et al. «Two-Carbon Ring Expansion of Bicyclic Aziridines to Oxazocines via Aryne Insertion into a σ C–N Bond». Chemical Science, vol. 16, n.o 43, 2025, pp. 20368-75. DOI.org (Crossref), https://doi.org/10.1039/D5SC04998A.
NO University of Wisconsin-Madison
NO Agencia Estatal de Investigación (España)
NO Ministerio de Ciencia e Inovación (España)
DS Docta Complutense
RD 18 mar 2026