Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 48, Pages 9826-9830Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob02159h
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Funding
- National Research Foundation [NRF-2020R1F1A1068452, NRF-2020R1A4A2002831]
- Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC) - Korea government (Ministry of Education) [2019R1A6C1010042]
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A Pd-catalyzed asymmetric [5 + 2] cycloaddition reaction was developed for the synthesis of N-fused 1,3-oxazepines using vinylethylene carbonates and sulfamate-derived cyclic imines. Under mild reaction conditions, a series of optically active N-fused 1,3-oxazepines were synthesized in good yields (up to 89%) and enantioselectivities (up to 90 : 10 er), indicating this method as a straightforward approach to enantiomerically enriched 1,3-oxazepine derivatives. The synthetic utility of the presented reaction was further demonstrated by the successful transformation of the resulting 1,3-oxazepines to useful polycyclic N-fused 1,3-oxazepanes.
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