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 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 reduc...

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Published inChemical & pharmaceutical bulletin Vol. 44; no. 10; p. 1812
Main Authors AOYAGI, Yutaka, MAEDA, Mikiko, MORO, Akira, KUBOTA, Ken, FUJII, Yohko, FUKAYA, Haruhiko, OHTA, Akihiro
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.10.1996
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Summary: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).
ISSN:0009-2363
1347-5223