Highly regioselective synthesis of amino-functionalized dendritic polyglycerols by a one-pot hydroformylation/reductive amination sequence
Highly regioselective synthesis of amino-functionalized dendritic polyglycerols by a one-pot hydroformylation/reductive amination sequence
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DOI：
10.1021/jo0481304
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发表时间：
2005-03-18
影响因子：
3.6
通讯作者：
Haag, R
中科院分区：
文献类型：
--
作者：
Koç, F;Wyszogrodzka, M;Haag, R
具有中性核心结构和壳中胺基的树枝状结构是一个合成挑战，并且需要有效的访问。在本文中，高选择性Rh-催化剂用于树枝状全烯丙基化聚甘油1与各种胺在一锅法中的顺序氢化/还原胺化，以高产率（73-99%）得到树枝状多胺3a-e。在所有情况下，都观察到烯丙基醚和醛中间体的完全转化。此外，使用受保护的胺在脱保护后提供反应性核-壳型结构。这些可溶性但膜可过滤的多功能树枝状多胺作为合成中的试剂或作为均相催化中的支持物以及用于DNA转染的非病毒载体是高度感兴趣的。
[GRAPHICS]Dendritic architectures with neutral core structures and amines groups in the shell are a synthetic challenge, and there is a need for an efficient access. In this paper, highly selective Rh-catalysts are used for sequential hydroformylation/reductive amination of dendritic perallylated polyglycerols 1 with various amines in a one-pot procedure to give dendritic polyamines 3a-e in high yields (73-99%). In all cases, complete conversion of the allyl ether and aldehyde intermediate has been observed. Furthermore, the use of protected amines provides reactive core-shell-type architectures after deprotection. These soluble but membrane filterable multifunctional dendritic polyamines are of high interest as reagents in synthesis or as supports in homogeneous catalysis as well as nonviral vectors for DNA-transfection.