Chiral Cyclopropenimine-catalyzed Asymmetric Michael Addition of Bulky Glycine Imine to α,β-Unsaturated Isoxazoles

A highly efficient asymmetric Michael addition of bulky glycine imine to alpha,beta-unsaturated isoxazoles has been achieved by using 5 mol% of chiral cyclopropenimine as a chiral organo-superbase catalyst under mild conditions. Michael adducts were obtained in excellent yields (up to 97%) and stereoselectivities (up to> 99:1 dr and 98% ee). A significant solvent effect was found in these chiral organosuperbase catalyzed asymmetric Michael reactions. Gram-scale preparation of Michael adducts and their transformations are realized to provide corresponding products without loss of stereoselectivities. The configurations of Michael adduct was determined by single-crystal X-ray diffraction analysis.

Automated summary

A highly efficient asymmetric Michael addition of bulky glycine imine to alpha,beta-unsaturated isoxazoles has been achieved using a chiral cyclopropenimine catalyst, resulting in high yields and stereoselectivities. Solvent choice was found to have a significant effect on the reaction, and gram-scale preparation and transformations of the Michael adducts were accomplished without loss of stereoselectivity.