A Regioselective Cyclohexannulation Procedure <i>via</i> Dienamine [4 + 2] Cycloaddition. Synthesis of Functionalised Decalins

Abstract

Abstract A regioselective cyclohexannulation procedure, whose key step involves the [4 + 2] cycloaddition of dienamines 12–24 with methyl acrylate, allows the conversion of cycloalkanones 1–11 to bicyclic dienoates 25 – 37 . The chemistry of 26 is briefly examined and, in the context of organoleptic studies concerning functionalised 5,5,9‐tri‐methyldecalins, the transformation of 37 to ketones 44 and 46 as well as to acetates 53–56 is described.