Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis

The preparation and use of alpha-(acyloxy)alkyl xanthates to generate and capture alpha-(acyloxy)alkyl radicals is briefly reviewed. Their inter- and intramolecular additions to both activated and unactivated, electronically unbiased, alkenes, and to (hetero)aromatic rings, as well as their radical allylation and vinylation reactions are described. Application to the total synthesis of two 4-hydroxytetralone natural products is also presented.

Automated summary

The preparation and use of alpha-(acyloxy)alkyl xanthates for generating and capturing alpha-(acyloxy)alkyl radicals are reviewed. The article describes their inter- and intramolecular additions to various alkenes and aromatic rings, as well as their radical allylation and vinylation reactions. The application of these reactions in the total synthesis of two 4-hydroxytetralone natural products is also presented.