Ruthenium-Catalyzed Multicomponent Reactions: Access to -Silyl--Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes

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 si...

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Bibliographic Details
Published inChemistry : a European journal Vol. 22; no. 8; pp. 2634 - 2638
Main Authors Trost, Barry M., Koester, Dennis C., Sharif, Ehesan U.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.02.2016
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ruthenium
KETONES
COMPLEX
stereoselectivity
ENANTIOSELECTIVE SYNTHESIS
dienes
HYDROSILYLATION
silanes
catalysis
ALDEHYDES
ASYMMETRIC PROPARGYLATION
ALKYNES
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Summary: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.
Bibliography:NIH RePORTER
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201504981