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- Title
Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene–Alkyne Coupling.
- Authors
Trost, Barry M.; Koester, Dennis C.; Herron, Alastair N.
- Abstract
The synthesis of vinyl boronates and vinyl silanes was achieved by employing a Ru-catalyzed alkene–alkyne coupling reaction of allyl boronates or allyl silanes with various alkynes. The double bond geometry in the generated vinyl boronates can be remotely controlled by the juxtaposing boron- and silicon groups on the alkyne substrate. The synthetic utility of the coupling products has been demonstrated in a variety of synthetic transformations, including iterative cross-coupling reactions, and a Chan-Lam-type allyloxylation followed by a Claisen rearrangement. A sequential one-pot alkene-alkyne-coupling/allylation-sequence with an aldehyde to deliver a highly complex α-silyl-β-hydroxy olefin with a handle for further functionalization was also realized.
- Subjects
BORONIC acids; VINYLATION; SILANE compounds; CHEMICAL synthesis; RUTHENIUM catalysts; ALKENES; ALKYNES; COUPLING reactions (Chemistry); STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 52, p16089
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201509238