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Indium trichloride mediated cleavage of acetonides in the presence of acid-labile functional groups; enhancing the synthetic utility of 1,3-dioxolanyl-substituted 1,2-oxazines.

  作者 Pfrengle, Fabian;Dekaris, Vjekoslav;Schefzig, Luise;Zimmer, Reinhold;Reissig, Hans-Ulrich;  
  选自 期刊  SYNLETT;  卷期  2008年-19;  页码  2965-2968  
  关联知识点  
 

[摘要]InCl3 in an MeCN-H2O mixt. chemoselectively cleaved the isopropylidene acetals of various 1,3-dioxolanyl-substituted 1,2-oxazines as well as carbohydrate derivs. Deprotection of acetonides can be achieved in substrates susceptible for acid-induced cyclizations. Most importantly, enol ether moieties are not attacked and the presence of glycosidic linkages or acid-sensitive protecting groups such as Me3CMe2Si, Me3Si(CH2)2, or Me3CO2C is also tolerated.

 
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