Work

An Aza‐Prilezhaev‐Based Method for Inversion of Regioselectivity in Stereospecific Alkene 1,2‐Aminohydroxylations

Year: 2024

Type: 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 S N 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.

Source: Angewandte Chemie

DOI: 10.1002/ange.202409836

Authors: Wenbin Tu, Joshua J. Farndon, Craig M. Robertson, John F. Bower

Institutions: University of Liverpool, University of Bristol

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,250

Funders: China Scholarship Council, Engineering and Physical Sciences Research Council