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Synlett 2001; 2001(11): 1747-1750
DOI: 10.1055/s-2001-18100
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Diastereoselective Allylation of a Chiral Imine with Allylzinc Reagents: Diastereoselective Synthesis of a Novel Broad Spectrum Carbapenem

Yuichi Sugimoto* , Hideaki Imamura, Hiroki Sakoh, Koji Yamada, Hajime Morishima
  • *Banyu Tsukuba Research Institute, Okubo-3, Tsukuba 300-2611, Ibaraki, Japan; Fax + 81(298)77 20 27; E-mail: sugmtoyt@banyu.co.jp
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Publication Date:
29 October 2001 (online)

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Diastereoselective allylation of chiral imine with allylmetal reagents was applied to prepare β-amino acid derivative as a key intermediate for the synthesis of a novel carbapenem 1. Combination of the allylzinc reagents and chiral imine, which was derived from l-valine methyl ester as a chiral auxiliary afforded a homoallylamine in good yield with excellent diastereoselectivity.

diastereoselective allylation - chiral imine - homoallylamine - 1-β-methylcarbapenem

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