Transformation of Alkyl N-(Vinyloxy)benzimidates to Alkyloxazoles. Mechanism and Extension

Article abstract of DOI:10.1246/bcsj.67.2219

Transformation of alkyl N-(vinyloxy)benzimidates to alkyloxazoles proceeds through the intermediates: a charge-separated 1,2-oxazetidine derivative and then 1-hydroxy-2-<imino>maleic acid diester, while their photochemical transformation takes place via a concerted <1.3> sigmatropic shift.As the extension of this reaction, the preparation of the precursor proposed for virginiamycin M2 synthesis and the reaction of N-analogs of alkyl N-(vinyloxy)benzimidates are described.