AI Article Synopsis
- Under acidic conditions with TFA and water, BocNHOTs facilitates specific 1,2-aminohydroxylation of alkenes through a two-step reaction involving aziridination and water-mediated opening.
- This method leads to different or more selective regioselectivity compared to traditional epoxidation methods.
- The reaction can be adapted to use various nucleophiles, enabling diverse transformations like amino(thio)etherification, diamination, and more, as well as unique intramolecular reactions.
Article Abstract
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 S2 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.
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| http://dx.doi.org/10.1002/anie.202409836 | DOI Listing |
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An Aza-Prilezhaev-Based Method for Inversion of Regioselectivity in Stereospecific Alkene 1,2-Aminohydroxylations.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD.
Article Synopsis
- Under acidic conditions with TFA and water, BocNHOTs facilitates specific 1,2-aminohydroxylation of alkenes through a two-step reaction involving aziridination and water-mediated opening.
- This method leads to different or more selective regioselectivity compared to traditional epoxidation methods.
- The reaction can be adapted to use various nucleophiles, enabling diverse transformations like amino(thio)etherification, diamination, and more, as well as unique intramolecular reactions.
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