A facile synthesis of polysubstituted pyrroles.
alpha-Aminoalkylcuprates prepared from CuX.2LiCl (X = Cl, CN) and 1 equiv of an alpha-lithiocarbamate undergo conjugate addition reactions to alpha,beta-alkynyl ketones in moderate to good yields, affording E:Z mixtures of alpha,beta-enones. Treatment of the conjugate adducts with PhOH/TMSCl in CH(2)Cl(2) effected carbamate deprotection and cyclization to afford a flexible two-step synthesis of substituted pyrroles.
Howard L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA. dieterr@clemson.edu
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D002219:Carbamates / Q000737:chemistry / Q000378:metabolism; D003300:Copper / Q000737:chemistry / Q000378:metabolism; D003500:Cyclization; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D002219:Carbamates; D011758:Pyrroles; D003300:Copper