Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 35, Pages 11998-12003Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201906283
Keywords
boron; copper; enantioselective catalysis; fluorine; synthetic methods
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Funding
- Japan Society for the Promotion of Science (JSPS) through KAKENHI [18H03907, 17H06370, 19K15547]
- NIH [GM-130395]
- JSPS [18J20858]
- Shanghai Institute of Organic Chemistry
- Institute for Chemical Reaction Design and Discovery (ICReDD)
- Grants-in-Aid for Scientific Research [18J20858] Funding Source: KAKEN
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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 either a Z- or E-allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z/E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.
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