Enantioselective conjugate addition of rationally designed chiral cuprate reagents to 2-cycloalkenones

EJ Corey, R Naef, FJ Hannon

Index: Corey, E. J.; Naef, Reto; Hannon, Francis J. Journal of the American Chemical Society, 1986 , vol. 108, # 22 p. 7114 - 7116

Full Text: HTML

Citation Number: 136

Abstract

Since even small amounts of alkoxide impurities are deleterious to enantioselectivity, it was decided to add to the reagent a substance which might destroy alkoxide and then to add enone. Good results were obtained by using methyl iodide as an alkoxide scavenger with the following sequential stoichiometric protocol: 1.0 equiv of amino alcohol 1; 0.89 equiv of RLi; 0.18 equiv of CHJ; 0.67 equiv of CUI; 0.45 equiv of RLi; 0.09 equiv of CH31; 0.30 ...