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Catalytic Enantioselective Synthesis of Allylic Boronates with a Trisubstituted Alkenyl Fluoride and Conversion to Compounds with a F-Substituted Stereogenic Quaternary Center.

08:00 EDT 13th June 2019 | BioPortfolio

Summary of "Catalytic Enantioselective Synthesis of Allylic Boronates with a Trisubstituted Alkenyl Fluoride and Conversion to Compounds with a F-Substituted Stereogenic Quaternary Center."

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
Z:
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.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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