Xanthate-Based Pathways to Ketones

This brief review describes applications of the radical chemistry of xanthates developed in the author's laboratory for the synthesis of open-chain and cyclic ketones. Most direct and general are additions of α-ketonyl xanthates to alkenes, but β-ketonyl and S-acyl-xanthates are also valuable reagents. Several novel allylation reactions can be used in conjunction with xanthates to provide a variety of ketones. The radical addition step can then be followed by various radical and non-radical post-modification steps to furnish more elaborate compounds. This chemistry is flexible, versatile, highly tolerant of numerous functional groups, and, importantly, allows intermolecular additions to be accomplished on non-activated, electronically unbiased alkenes. These properties open synthetic pathways and retrosynthetic analyses hitherto unavailable.