An Aza‐Prilezhaev‐Based Method for Inversion of Regioselectivity in Stereospecific Alkene 1,2‐Aminohydroxylations
Under acidic conditions (TFA) and in the presence of water, BocNHOTs promotes stereospecific 1,2-aminohydroxylations of alkenes. The processes involve intermolecular aza-Prilezhaev aziridination followed by stereospecific S<sub>N</sub>2 opening by water. This reagent combination provides regiochemical outcomes that are opposite to, or more selective than those observed using epoxidation initiated 1,2-aminohydroxylation protocols. Replacement of water by other nucleophiles allows 1,2-amino(thio)etherification, diamination, aminoazidation and aminofluorination reactions. Intramolecular processes are also feasible, including unusual variants that evoke azabicyclobutane-like reactivity.
Authors
- Joshua J. Farndon
- John F. Bower (ORCID: https://orcid.org/0000-0002-7551-8221)
- Wenbin Tu
- Craig M. Robertson (ORCID: https://orcid.org/0000-0002-4789-7607)
Institutions
- University of Liverpool (GB)
- University of Bristol (GB)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2024-08-22
- DOI
- https://doi.org/10.1002/anie.202409836
- Citations
- 14
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- China Scholarship Council
- Engineering and Physical Sciences Research Council