An Alternative Reaction Outcome in the Gold-Catalyzed Rearrangement of 1-Alkynyloxiranes

作者:Gonzalez Maria J; Gonzalez Jesus; Vicente Ruben*
来源:European Journal of Organic Chemistry, 2012, 2012(31): 6140-6143.
DOI:10.1002/ejoc.201201191

摘要

The gold(III)-catalyzed rearrangement of tetrasubstituted 1-alkynyloxiranes is described. This transformation led to a different reaction outcome with respect to related substrates previously studied. Thus, tertiary a-alkynylketones or alkynols can be selectively obtained. Moreover, gold(III) proved capable to catalyze the rearrangement of simple epoxides. These results indicate that gold(III) complexes act as oxophilic Lewis acids rather than p-acids in these transformations.

  • 出版日期2012-11