(E)- and (Z)-β-borylallylsilanes by alkyne silaboration followed by regio- and stereoselective double-bond migration.

Angew Chem Int Ed Engl

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

Published: December 2011

AI Article Synopsis

  • β-Borylallylsilanes are created through a two-step process involving the silaboration of terminal alkynes and a palladium-catalyzed migration.
  • The migration of the double bond in the β-borylalkenylsilanes is regioselective and can be manipulated by using different additives.
  • This method allows for the production of both (E)- and (Z)-β-borylallylsilanes, showcasing the ability to control stereochemistry in the synthesis.

Article Abstract

Double take: β-Borylallylsilanes have been synthesized by the regioselective silaboration of terminal alkynes followed by palladium-catalyzed double-bond migration of the resulting β-borylalkenylsilanes. The stereoselectivity of the double-bond migration can be controlled by additives, thus leading to the stereocomplementary synthesis of (E)- and (Z)-β-borylallylsilanes.

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http://dx.doi.org/10.1002/anie.201106077DOI Listing

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