Chiral Catalyst for Enantioselective Reactions of Aryl- and Styryldiazoacetates


Catalysis of highly enantioselective cyclopropanations, tandem cyclopropanation/Cope rearrangements and combined C-H functionalization/Cope rearrangement reactions.

Key Benefits

  • Exhibits good tolerance to large ester groups for electron-withdrawing in high asymmetric induction.
  • Efficient reactions in dichlormethane allowing broader range of substrates than other enantioselective catalyst.

Technical Summary

Researchers have sought a chiral dirhodium catalyst for use in reactions involving diazo compounds; these reactions rely heavily on the ability of a catalyst to drive the production of one enantiomer over another. One of the current standard catalysts used in this field is the compound Rh2(S-DOSP)4. This compound is effective, but its yield and efficiency are highly dependent upon the solvent and substrate structure. The newly developed catalyst is comparable to Rh2(S-DOSP)4 in yield and efficiency under various testing conditions, but exhibits far superior consistency in these metrics. Testing conditions included alterations of the solvent, temperature, and molarity of solution (amount of molecules of substrate per volume of solvent). This new catalyst is more robust than Rh2(S-DOSP)4 in that the new catalyst works more efficiently in a wider variety of solvents, even when the desired reactant is only present in low concentrations.

Patent Information

App Type Country Serial No. Patent No. File Date Issued Date Patent Status
Nationalized PCT - United States United States 14/123,389 8,975,428 12/2/2013 3/10/2015 Issued
Tech ID: 11151
Published: 6/30/2011