Synthesis of N-protected allylic amines from allyl ethers

被引：25

作者：

Kim, JD ^{[1
]}

Lee, MH ^{[1
]}

Han, G ^{[1
]}

Park, H ^{[1
]}

Zee, OP ^{[1
]}

Jung, YH ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 39期

基金：

新加坡国家研究基金会;

关键词：

chlorosulfonyl isocyanate; allylic amine; N-allylcarbamate; allyl ether;

D O I：

10.1016/S0040-4020(01)00822-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (N) 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. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8257 / 8266

页数：10

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