Synthesis of N-protected allylic amines from allyl ethers

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 t...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 39; pp. 8257 - 8266
Main Authors Kim, Ji Duck, Lee, Min Hee, Han, Gyoonhee, Park, Hyunju, Zee, Ok Pyo, Jung, Young Hoon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.09.2001
Elsevier
Subjects
allyl ether
allylic amine
Chemistry
Chemistry, Organic
chlorosulfonyl isocyanate
N-allylcarbamate
Physical Sciences
Science & Technology
allyl ether
allylic amine
chlorosulfonyl isocyanate
N-allylcarbamate
ASYMMETRIC-SYNTHESIS
ACID
STEREOCHEMISTRY
STEREOSELECTIVE PREPARATION
COPPER
REARRANGEMENT
ALCOHOLS
AMINATION
ORGANOMETALLIC REAGENTS
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Summary: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. A synthetic method for N-protected allylic amines from allyl ethers using chlorosulfonyl isocyanate (CSI) is presented.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00822-5