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Synfacts 2005(1): 0172-0172  
DOI: 10.1055/s-2005-872220
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthetic Procedure for Azidoalcohols Utilizing Polymer-Supported Reagent

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
E. C. S. Brenelli*, J. A. Brenelli, R. C. L. Pinto
Universidade Federal Fluminense, Brazil
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

β-Azidoalcohols were prepared from α-haloketones by using polystrene-based azide (PS-azide) and borohydride exchange resin (PS-BER) (20 examples). The azidations of α-haloketones 1 were carried out in the presence of PS-azide exchange resin at 30 °C for 30 minutes to give the corresponding α-azidoketones 2 in 68-95% yields. The resulting α-azidoketones 2 were reduced with PS-BER at 30 °C for 30 minutes to give α-aryl-β-azidoalcohols 3 in 78-96% yields.