Catalytic Enantioselective Synthesis of <i>anti</i>‐Vicinal Silylboronates by Conjunctive Cross‐Coupling
Yan Meng, Ziyin Kong, James P. Morken
Abstract
Chiral 1,2-bimetallic reagents are useful motifs in synthetic chemistry. Although syn-1,2-bimetallic compounds can be prepared by alkene dimetallation, anti-1,2-bimetallics are still rare. The stereospecific 1,2-metallate shift that occurs during conjunctive cross-coupling is shown to enable a practical and modular approach to the catalytic synthesis of enantioenriched anti-1,2-borosilanes. In addition to reaction development, the synthetic utility of anti-1,2-borosilanes was investigated, including applications to the synthesis of anti-1,2-diols and anti-1,2-amino alcohols.
Topics & Concepts
Enantioselective synthesisBimetallic stripVicinalAlkeneCatalysisChemistryStereospecificityReagentCombinatorial chemistryStereochemistryOrganic chemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCoordination Chemistry and Organometallics