ALKENYL COPPER REAGENTS-18; CARBOCUPRATION OF ACETYLENIC ACETALS AND KETALS; SYNTHESIS OF MANICONE, GERANIAL AND 2,4(E,Z)-DIENALS

Article abstract of DOI:10.1016/S0040-4020(01)91100-7

Lithium diorganocuprates add across the triple bond of substituted and non-substituted acetylenyl acetals and ketals to give dialkenylcuprates, which can be decomposed into alkoxyallenes or may be trapped with a variety of electrophiles, such as alkyl, alkenyl, alkynyl and aryl halides.They may also undergo conjugate addition to α-β unsaturated esters and ketons.The method is used for the synthesis of (+/-)-manicone, pure geranial and (E,Z)2,4-dienals.