Synthesis of N-protected allylic amines from allyl ethers

Ji Duck Kim, Min Hee Lee, Gyoonhee Han, Hyunju Park, Ok Pyo Zee, Young Hoon Jung

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Abstract

A synthetic method for N-protected allylic amines from allyl ethers using chlorosulfonyl isocyanate (CSI) is presented. The reaction of 4-phenylbut-2-enyl methyl ether (1i) with CSI afforded methyl N-(1-benzylallyl)carbamate (2i) and methyl N-(4-phenylbut-2-enyl)carbamate (3i) in a 1:1.1 ratio. On the other hand, 1-benzylallyl methyl ether (1k) afforded the same products in a 4.6:1 ratio. The reactions of 1,4-diphenylbut-2-enyl methyl ether (1p) and (1-benzylcinnamyl) methyl ether (1q) with CSI gave only one product, methyl N-(1-benzylcinnamyl)carbamate (2p), due to the steric hindrance of the phenyl ring and the formation of a stable conjugated product. We also examined the reactions of diene ethers (4) with CSI.

Original languageEnglish
Pages (from-to)8257-8266
Number of pages10
JournalTetrahedron
Volume57
Issue number39
DOIs
Publication statusPublished - 2001 Sep 24

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kim, J. D., Lee, M. H., Han, G., Park, H., Zee, O. P., & Jung, Y. H. (2001). Synthesis of N-protected allylic amines from allyl ethers. Tetrahedron, 57(39), 8257-8266. https://doi.org/10.1016/S0040-4020(01)00822-5