CYCLIC AND ACYCLIC PRODUCTS FROM THE ADDITION OF 1-AZA-ALLYL ANIONS TO DIENES AND ALPHA,BETA-UNSATURATED KETONES - REGIOSELECTIVITY

Addition of 1-aza-allyl-lithium compound 1 to isoprene at low temperature yields two regioisomeric gamma,delta-unsaturated imines 3, whereas at THF reflux temperature the cyclic regioisomeric cyclohexene derivatives 4 are formed. With 2,3-dimethylbutadiene, the acyclic products 6 are obtained. C-C-bond formation also takes place with methylvinylketone, leading to the acyclic regioisomers 7,8 from 1,2- and 1,4 attack.