Remarkable switch of regioselectivity in epoxide ring opening of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane with amines: practical synthesis of trans-4-amino-3-hydroxypiperidines and trans-3-amino-4-hydroxypiperidines
Remarkable switch of regioselectivity in epoxide ring opening of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane with amines: practical synthesis of trans-4-amino-3-hydroxypiperidines and trans-3-amino-4-hydroxypiperidines
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DOI：
10.1016/j.tetlet.2010.03.061
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发表时间：
2010-05-26
影响因子：
1.8
通讯作者：
Kurimoto, Isao
中科院分区：
文献类型：
--
作者：
Tokuda, Osamu;Aikawa, Toshiaki;Kurimoto, Isao
本文报道了一种简便、高选择性的3，4-环氧哌啶开环反应方法。我们还描述了使用相同的N-烷基取代的3，4-环氧哌啶的C4选择性开环方法的实际改进。该方法提供了以简单的程序获得药学上相关的反式-3-氨基-4-羟基哌啶和反式-4-氨基-3-羟基哌啶的途径。(C)2010爱思唯尔有限公司保留所有权利。
A simple and highly C3 selective ring-opening method for 3,4-epoxypiperidines has been developed. We also describe a practical improvement of the C4 selective ring-opening method using the same N-alkyl substituted 3,4-epoxypiperidines. This method provides access to pharmaceutically relevant trans-3-amino-4-hydroxypiperidines and trans-4-amino-3-hydroxypiperidines with simple procedures. (C) 2010 Elsevier Ltd. All rights reserved.