Nucleophilic selenium

Since Sharpless' application of a nucleophilic selenolate to the ring openi ng of epoxides, various nucleophilic selenium species have been widely used in organic synthesis. Advantages of the use of selenolates are rationalize d in their high reactivity and selectivity as well as in the easy removal o f the selenium moiety from the reaction products. In this chapter, the typi cal methods of preparing nucleophilic selenium species, their reactions wit h various organic substrates, and the utility of selenium reagents which ha ve a selenium to main group element bond as an alternative source to the nu cleophilic selenium are summarized. In addition, applications of nucleophil ic selenium to asymmetric and solid-phase syntheses are presented separatel y These new attempts are further increasing the intriguing utility of the n ucleophilic selenium species.