Method for the synthesis of axially chiral organoboron compounds
AssigneeLaboratory for Synthetic Chemistry and Chemical Biology Limited
InventorsYifan PING, Chi-Ming CHE
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Abstract
A highly efficient and atroposelective Rh-catalyzed [2+2+2] cycloaddition for the synthesis of axially chiral aryboron compounds is developed. The reactions of diynes and alkynylborons smoothly occur in an atom-economical manner, affording a variety of C—B atropisomers in excellent yields and enantioselectivities. The protocol features mild conditions, broad substrate scope, and good functional tolerance. The obtained C—B atropisomers show powerful synthetic applications in terms of producing novel chiral phosphine ligands.
Claims11
A compound represented by the following formula:
- wherein R is selected from phenyl or cyclohexyl;
- wherein X is selected from N-tosyl,
- wherein R1 is selected from substituted or unsubstituted (C1-4)alkyl, benzyl,
- wherein R2 is selected from methyl or ethyl;
- wherein R3 is selected from substituted or unsubstituted (C1-5)alkyl, substituted or unsubstituted (C1-5)alkenyl, phenyl, or cyclopropane;
- and
- wherein Y is selected from
In a method for synthesizing axially chiral aromatic organoboron compounds, the improvement comprising reacting a boron-containing organic precursor material and a branched linear organic precursor material in the presence of a rhodium catalyst and a chiral ligand.
Dependencies are inferred from the claim text.