Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 8, Pages 2634-2638Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504981
Keywords
catalysis; dienes; ruthenium; silanes; stereoselectivity
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Funding
- National Science Foundation [CHE-1360636]
- National Institutes of Health [GM 033049]
- Alexander von Humboldt-Foundation
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The synthesis of densly functionized -silyl--hydroxyl vinylsilanes via ruthenium-catalyzed multicomponent reaction (MCR) is reported herein. Exceptionally high regio- and diastereoselectivity was achieved by employing an unprecedented hydrosilylation of bifunctional silyl-propargyl boronates. The simple protocol, mild reaction conditions, and unique tolerability of this method make it a valuable tool for the synthesis of highly elaborated building blocks. The one-pot synthesis of stereodefined olefins, the generation of a valuable cyclohexene building block through a four-component MCR, and further functionalization in an abundance of diastereoselective reactions is disclosed herein.
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