Conjugate addition reactions of alpha-aminoalkylcuprates with alpha,beta-alkenyl-, alpha,beta-alkynyl-, alpha,beta-beta,gamma-allenyl-, and alpha,beta-gamma,delta-dienyl carboxylie acid derivatives, nitriles, and sulfoxides

alpha -Aminoalkylcuprates prepared from alpha -lithio carbamates and CuCN.2 LiCl participate in 1,4-addition reactions with alpha,beta -unsaturated est ers, thiol esters, imides, and nitriles in poor to excellent yields dependi ng upon the electron-withdrawing substituent and the substitution pattern o f the unsaturated substrate. These reagents also undergo conjugate addition reactions with alpha,beta -alkynyl esters, sulfoxides, and nitriles and wi th alpha,beta-beta,gamma -unsaturated allenyl esters. Excellent stereocontr ol is achieved in the conjugate additions of alpha -aminoalkylcuprates to t he allenyl eaters, while poor stereoselectivity results in the conjugate ad ditions to the alkynyl derivatives. Deprotection and cyclization of the alk ynyl adducts affords pyrrolin-2-ones, while similar treatment of the alleny l adducts affords 4-alkylidine- pyrrolidin-2-ones and pyrrolizidinones.