Divergent Synthesis of Enantioenriched β‑FunctionalAmines via Desymmetrization of meso -Aziridines withIsocyanides
2019
A highly enantioselective ring-opening desymmetrization of meso-aziridines with isocyanides was achieved in the presence of a chiral N,N′-dioxide/Mg(OTf)2 complex. The in situ generated chiral 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous H2O and TMSN3, enabling a collective synthesis of various chiral vicinal amino-oxazoles, spiroindolines, β-amino amides, and tetrazole derivative in moderate to high yields with excellent enantioselectivities.
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