Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis |
| |
Authors: | Christie Morrill |
| |
Affiliation: | Contribution from the Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA |
| |
Abstract: | Tri-substituted vinyl pinacol boronates, which are key reactive intermediates in a variety of transformations, are synthesized using ruthenium-catalyzed olefin cross-metathesis of α-substituted vinyl boronates and various alkenes. Cross-metathesis of 2-isopropenyl pinacol boronate proceeds with moderate yield and high Z-selectivity when sterically unhindered cross partners are used. Cross-metathesis of vinyl boronates that possess α-substitution larger than a methyl group is also achieved. Yield and Z-selectivity are lower in these cases, and the success of a cross-metathesis reaction is highly dependent on the steric bulk surrounding the double bond of the α-substituted vinyl boronate. |
| |
Keywords: | Olefin cross-metathesis Vinyl boronates Tri-substituted alkenes Ruthenium catalysis |
本文献已被 ScienceDirect 等数据库收录! |
|