SAMARIUM(II) IODIDE-MEDIATED INTERMOLECULAR COUPLING REACTIONS OF N,N-DIBENZYLENAMIDES WITH CARBONYL-COMPOUNDS AND TRANSFORMATION OF THE PRODUCT, N,N-DIBENZYL-GAMMA-HYDROXYAMIDE TO DELTA-AMINOALCOHOL

Samarium(II) iodide-mediated intermolecular coupling reactions of N,N- dibenzylenamides (1a-d) with carbonyl compounds (2a-i) produced the co rresponding N,N'-dibenzyl-gamma-hydroxyamides (3a-i) in moderate to go od yields. Attempts to remove the two benzyl groups of 3a using hydrog enolysis and Birch reduction were unsuccessful, On the other hand, the lithium aluminum hydride reduction of 3a produced 10 in 61% yield, an d dedibenzylation using 20% Pd(OH)(2) on carbon gave the corresponding delta-aminoalcohol(11).