Samarium(II) iodide-mediated intermolecular coupling reactions of N,N- dibenzylenamides with carbonyl compounds and transformation of the product, N,N-dibenzyl-γ-hydroxyamide to δ-aminoalcohol

Article abstract of DOI:10.1248/cpb.44.1812

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

Full text of DOI:10.1248/cpb.44.1812

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