Stannyl anions epoxides

Lithiated epoxides are more commonly trapped by electrophiles, generating elaborated oxiranes. In this arena, Hodgson and co-workers <04OL4187> have optimized the lithiation of non-stabilized terminal epoxides with iec-hutylhthium assisted by diamine ligands, such as dibutylbispidine (DBB, 99) or (-)-sparteine 100. The oxiranyl anions thus formed engage in smooth nucleophilic addition onto aldehydes to form epoxyalcohols e.g., 101) the same conditions can be used for the stannylation of epoxides e.g., 84 102). Similarly,... 

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