Journal of Organic Chemistry 2006-10-27

Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.

David M Hodgson, Bogdan Stefane, Timothy J Miles, Jason Witherington

Index: J. Org. Chem. 71 , 8510, (2006)

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Abstract

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.