Preparation and reactions of 2-zincated 2-cyclohexen-1-one and related heterocycles

Article abstract of DOI:10.1016/s0040-4020(97)10116-8

The reaction of zinc dust in THF with 2-iodocyclohexenone 6, 3-iodo-N- benzoyl-l-azacyclohex-2-en-4-one 8 provides the corresponding zinc organometallics 3 and 4 which react in the presence of a copper(I) catalyst or palladium(O) catalyst with an allylic bromide or alkenyl and aryl iodides in satisfactory to good yields. Several of these products can further be cyclized leading diastereoselectively to a polyfunctional decaline 12 or a pyrrole derivative 13. A 6-zincated uracil reagent has also been prepared and reacted with aryl iodides in the presence of a palladium catalyst leading to new 6-arylated uracil derivatives 11.