An investigation of silyl groups on asymmetric induction in a conjugate addition reactions with chiral n-silylamidocuprates

CHED 215

Stephen K. Cope, Steven H. Bertz, and Craig A. Ogle, cogle@uncc.edu. Department of Chemistry, University of North Carolina at Charlotte, Charlotte, NC 28223
Two classic chiral amines, Enders' RAMP (1) and Rossiter's S-MAPP(2), have been used as non-transferable ligands in organocuprate conjugate additions for the addition of n-butyl and methyl to chalcone and 2-cyclohexenone. These results will be compared to their silylated analogues 3, 4. Enantiomeric excesses of 90% and nearly quantitative chemical yields were observed in some cases for the silylated analogues.