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Synthesis 1996; 1996(8): 970-974
DOI: 10.1055/s-1996-4324
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Samarium(II) Iodide Mediated Intermolecular Coupling Reactions of N,N-Dibenzyl-α-haloamides with Carbonyl Compounds

Yutaka Aoyagi, Rie Asakura, Nobuko Kondoh, Rieko Yamamoto, Takeshi Kuromatsu, Ai Shimura, Akihiro Ohta*
  • *School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan, Fax +81(426)752605
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Publication Date:
31 December 2000 (online)

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Samarium(II) iodide mediated coupling reactions of α-haloamides with carbonyl compounds are found to give N,N-dibenzyl-β-hydroxyamides (4a-i, 5a-i, and 6a) in good yields under mild reaction conditions. The transformation of 4a and 5a to N,N-dibenzyl-3-phenylpropanamide (7) and β-hydroxycarboxylic acid (8), respectively, are described.

samarium(II) iodide - coupling reaction - α-haloamides - N,N-dibenzyl-β-hydroxyamide - β-hydroxycarboxylic acid

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