REGIOSPECIFIC CARBON-CARBON BOND FORMATION AT α AND β POSITIONS IN CYCLIC KETONES VIA DOUBLE MICHAEL ADDITION TO α-METHYLENE-β-ALKOXY CYCLIC KETONE

Article abstract of DOI:10.1016/0040-4039(81)80164-5

Very reactive 2-methylene-3-alkoxycyclohexanone was synthesized.The 1,4-conjugate addition of various nucleophiles to this enone gave only β'-alkylated 2-cyclohexenone with simultaneous elimination of the β-alkoxy group.The second 1,4-conjugate addition of other nucleophile to the resulting cyclohexenone leads to the α and β disubstituted ketones.