Oxiranyllithium reagents: Generation from organotin precursors, addition to aldehydes and ketones, and dimerization to α,α′-dialkoxyolefins

Article abstract of DOI:10.1016/S0040-4039(00)74841-6

Oxiranyllithium compounds can be generated from organotin precursors by tin-lithium exchange with butyllithium in THF at -90°C. In the presence of TMEDA, they react with aldehydes and ketones to give epoxy alcohols in good yields. In the absence of TMEDA, they dimerize to α,α′-dialkoxyolefins.