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Catalytic Enantioselective Synthesis of <i>anti</i>‐Vicinal Silylboronates by Conjunctive Cross‐Coupling

Yan Meng, Ziyin Kong, James P. Morken

2020Angewandte Chemie13 citationsDOI

Abstract

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
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