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Synlett 1995; 1995(7): 737-738
DOI: 10.1055/s-1995-5073
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Regio- and Stereocontrolled Iodocyclocarbamation of N-Carbamoyl-2,4-Dienylamine derivatives

Yoshiji Takemoto, Jun Takeuchi, Eiki Matsui, Chuzo Iwata*
  • *Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-Oka, Suita, Osaka 565, Japan, Fax +81 06 879 8214; internet iwata@phs.osaka-u.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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Mild iodo-catalyzed cyclocarbamations of N-benzyl-N-carbomethoxy-1-substituted-2,4-pentadienylamines were developed. The reactions proceed regio- and stereoselectively, giving rise to 4,5-trans-oxazolidin-2-ones bearing (E)-propenyl iodide at the C5 position as major products.

iodocyclocarbamation - 1,4-functionalization of 1,3-diene - N-Carbamoyl-1-substituted-2,4-Dienylamine - trans-oxazolidinone - β-hydroxy-ℇ-iodo-homoallylamine