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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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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Methyl Ethers
Ethers
Amines
Carbamates
chlorosulfonyl isocyanate

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
Kim, Ji Duck ; Lee, Min Hee ; Han, Gyoonhee ; Park, Hyunju ; Zee, Ok Pyo ; Jung, Young Hoon. / Synthesis of N-protected allylic amines from allyl ethers. In: Tetrahedron. 2001 ; Vol. 57, No. 39. pp. 8257-8266.
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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.",
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Kim, JD, Lee, MH, Han, G, Park, H, Zee, OP & Jung, YH 2001, 'Synthesis of N-protected allylic amines from allyl ethers', Tetrahedron, vol. 57, no. 39, pp. 8257-8266. https://doi.org/10.1016/S0040-4020(01)00822-5

Synthesis of N-protected allylic amines from allyl ethers. / Kim, Ji Duck; Lee, Min Hee; Han, Gyoonhee; Park, Hyunju; Zee, Ok Pyo; Jung, Young Hoon.

In: Tetrahedron, Vol. 57, No. 39, 24.09.2001, p. 8257-8266.

Research output: Contribution to journalArticle

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T1 - Synthesis of N-protected allylic amines from allyl ethers

AU - Kim, Ji Duck

AU - Lee, Min Hee

AU - Han, Gyoonhee

AU - Park, Hyunju

AU - Zee, Ok Pyo

AU - Jung, Young Hoon

PY - 2001/9/24

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N2 - 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.

AB - 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.

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