Parallel solution-phase syntheses of functionalised bicyclo[2.2.2]octanes:generation of a library using orchestrated multi-step sequences of polymer-supported reagents and sequesterants

An array of bicyclo[2.2.2]octane derivatives was prepared in high yield usi ng an orchestrated multi-step sequence of polymer-supported reagents and se questering agents, without any chromatographic purification steps. Nine int ermediate libraries were synthesised, with the final library possessing fiv e sites of diversity. Key steps included an efficient tandem Michael additi on reaction of acrylates with cyclohexenones and a subsequent reductive ami nation reaction.