Chemical and Pharmaceutical Bulletin p. 1812 - 1818 (1996)
Update date:2022-07-30
Topics:
Aoyagi, Yutaka
Maeda, Mikiko
Moro, Akira
Kubota, Ken
Fujii, Yohko
Fukaya, Haruhiko
Ohta, Akihiro
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).
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