An Aza-Prilezhaev-Based Method Inverts Regioselectivity in Stereospecific Alkene 1,2-Aminohydroxylations.
Angew Chem Int Ed Engl
; : e202409836, 2024 Aug 22.
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| MEDLINE
| ID: mdl-39171407
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 SN2 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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2024
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