One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols

Article abstract of DOI:10.1021/jo9521256

The reactions of 1,2- and 1,3-hydroxy azides with aldehydes under acidic conditions were examined. A variety of Lewis acids were examined, of which BF₃·OEt₂ was found the most convenient. Trimethylsilyl ether derivatives of the alcohols could also be reacted using trimethylsilyl triflate as the promoter. Twenty-five examples that proceed in moderate to quantitative yields are reported.