American Chemical Society
jo0615201_si_001.pdf (5.89 MB)

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

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journal contribution
posted on 2006-10-27, 00:00 authored by David M. Hodgson, Bogdan Štefane, Timothy J. Miles, Jason Witherington
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.