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The first catalytic method for diastereo- and enantioselective synthesis of allylic boronates bearing a Z-trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with a Z- or an E-allyldifluoride and is catalyzed by bisphosphine-Cu complexes, affording products in up to 99% yield, >98:2
E selectivity, and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible; notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluoro-substituted stereogenic quaternary center.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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