Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1138-1142Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811205
Keywords
allylation; allylic compounds; boron; ruthenium; stereoselective synthesis
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Funding
- JSPS KAKENHI [15H05756, 16K05694]
- JST [ACT-C] [JPMJCR12Z9]
- JSPS
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The stereoselective synthesis of anti isomers of gamma-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.
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