Resin-bound 4-phenyl-1,2-dihydroquinoline (DHQ): a new safety-catch linker for solid-phase organic synthesis (SPOS)

被引：21

作者：

Arseniyadis, S ^{[1
]}

Wagner, A ^{[1
]}

Mioskowski, C ^{[1
]}

机构：

[1] Univ Louis Pasteur Strasbourg 1, Fac Pharm, CNRS, UMR 7514,Lab Synth Bioorgan, F-67401 Illkirch Graffenstaden, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 10期

关键词：

D O I：

10.1016/j.tetlet.2003.12.161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new safety-catch linker has been developed for combinatorial solid-phase chemistry. Azidomethyl-polystyrene, obtained by nucleophilic Substitution of chloromethyl-polystyrene, undergoes an acid promoted Schmidt rearrangement. The resulting polymer-bound iminium participates in an aza Diels-Alder cycloaddition, which leads to a supported dihydroquinoline (DHQ resin). The acylated form of the DHQ resin is stable under basic, acidic and mild reducing agents. The cleavage proceeds in two steps (i) oxidative aromatization leading to an activated quinolinium and (ii) nucleophilic displacement of the quinoline resin. The overall process is high yielding and efficient. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：2251 / 2253

页数：3

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