Organolithium-Induced Alkylative Ring Opening of Aziridines: Synthesis of Unsaturated Amino Alcohols and Ethers

Organolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described.
The reactions were efficiently carried out with a variety of organolithiums, providing a promising new
strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derived aziridines
were prepared, and their propensity to undergo organolithium- induced alkylative desymmetrization is
detailed. Use of a single enantiomer of the latter aziridine provides a route to enantiopure unsaturated
amino ethers.