Construction of CF3-Containing Quaternary Chiral Centers via Michael Addition Reactions

Michael addition reactions of a variety of Grignard reagents to 4,4,4-trifluorinated alpha,beta-unsaturated carboxylic acid derivatives with 4-substituted oxazolidin-2-ones as a chiral auxiliary were found to occur smoothly in the presence of CuBr center dot SMe2 and TMSC1 to construct the desired products with the quaternary stereocenters possessing a CF3 group in good to excellent yields.

Automated summary

Using CuBr·SMe2 and TMSCl as catalysts, Michael addition reactions of various Grignard reagents to 4,4,4-trifluorinated alpha, beta-unsaturated carboxylic acid derivatives with 4-substituted oxazolidin-2-ones as a chiral auxiliary proceed smoothly to construct the desired products with quaternary stereocenters possessing a CF3 group in good to excellent yields.