Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 9, Pages 3849-3853Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b00535
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Funding
- Hong Kong Research Grants Council [153152/16P 153023/17P, C5023-14G]
- State Key Laboratory of Chemical Biology and Drug Discovery
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We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish gamma-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the C=C and C C bonds.
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