Journal
ACS CATALYSIS
Volume 6, Issue 7, Pages 4694-4698Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01400
Keywords
enantioselective; aziridine; palladium; heterocycles; desymmetrization
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Funding
- National Institute of General Medical Sciences of the National Institutes of Health [R15GM114766]
- National Science Foundation [CHE-1039784, CHE-0821552]
- University of North Carolina Wilmington
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Aziridines are important synthetic intermediates for the generation of nitrogen-containing molecules. N-Acylaziridines undergo rearrangement by ring expansion to produce oxazolines, a process known as the Heine reaction. The first catalytic, enantioselective Heine reaction is reported for meso-N-acylaziridines where a palladium(II)-diphosphine complex is employed. The highly enantioenriched oxazoline products are valuable organic synthons and potential ligands for transition-metal catalysis.
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