A Phosphane-Mediated Diastereoselective, Domino aza-Morita-Baylis-Hillman/Reduction Sequence Involving Water as Hydrogen Source

The new domino process disclosed here involves PBu3 as both a nucleophilic and a reducing agent. The process combines suitable electron-poor dienes, N-tosylimines, tri-n-butylphosphane and water. The final products formally result from reduction of vinylogous aza-MoritaBaylisHillman adducts. The reaction proceeds with an excellent stereochemical control of the relative configurations of the newly created contiguous carbon centres.