Cu‐Catalyzed Diastereo‐ and Enantioselective Reactions of γ,γ‐Disubstituted Allyldiboron Compounds with Ketones
Joseph M. Zanghi, Simon J. Meek
Abstract
A catalytic diastereo- and enantioselective method for the preparation of complex tertiary homoallylic alcohols containing a vicinal quaternary carbon stereogenic center and a versatile alkenylboronic ester is disclosed. Transformations are promoted by 5 mol % of a readily available copper catalyst bearing a bulky monodentate phosphoramidite ligand, which is essential for attaining both high dr and er. Reactions proceed with a wide variety of ketones and allylic 1,1-diboronate reagents, which enables the efficient preparation of diverse array of molecular scaffolds.
Topics & Concepts
StereocenterEnantioselective synthesisPhosphoramiditeCatalysisAllylic rearrangementChemistryDenticityVicinalLigand (biochemistry)ReagentCombinatorial chemistryOrganic chemistryMetalReceptorDNAOligonucleotideBiochemistryOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis