Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 17, Pages 5739-5743Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901251
Keywords
anthranils; asymmetric catalysis; cycloaddition; dearomatization; palladium
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Funding
- National Key R&D Program of China from MOST [2016YFA0202900]
- NSFC [21821002]
- Chinese Academy of Sciences [XDB20000000, QYZDY-SSW-SLH012]
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Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane-anthranil complex which has been confirmed by NMR experiments.
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