π-Allylpalladium formation from allylic amines via N,N-ditosylimides and N-tosylamides: Efficient synthesis of the antiviral agent carbovir

Article abstract of DOI:10.1021/jo00096a006

Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford π-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (±)-carbovir (1) from cyclopentadiene in only seven steps and 13% overall yield.