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

doi:10.1016/S0040-4020(01)00822-5

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 journal › Article › peer-review

24 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 language	English
Pages (from-to)	8257-8266
Number of pages	10
Journal	Tetrahedron
Volume	57
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4020(01)00822-5
Publication status	Published - 2001 Sept 24

Bibliographical note

Funding Information:
The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)00822-5

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title = "Synthesis of N-protected allylic amines from allyl ethers",

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.",

author = "Kim, {Ji Duck} and Lee, {Min Hee} and Gyoonhee Han and Hyunju Park and Zee, {Ok Pyo} and Jung, {Young Hoon}",

note = "Funding Information: The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998.",

year = "2001",

month = sep,

day = "24",

doi = "10.1016/S0040-4020(01)00822-5",

language = "English",

volume = "57",

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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

N1 - Funding Information: The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998.

PY - 2001/9/24

Y1 - 2001/9/24

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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U2 - 10.1016/S0040-4020(01)00822-5

DO - 10.1016/S0040-4020(01)00822-5

M3 - Article

AN - SCOPUS:0035944158

SN - 0040-4020

VL - 57

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JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -

Synthesis of N-protected allylic amines from allyl ethers

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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