Journal
ORGANIC LETTERS
Volume 21, Issue 15, Pages 6096-6101Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02242
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Funding
- National Natural Science Foundation of China [21801175]
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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, beta-amino amides, and tetrazole derivative in moderate to high yields with excellent enantioselectivities.
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