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

…, B Štefane, TJ Miles, J Witherington

Index: Hodgson, David M.; Stefane, Bogdan; Miles, Timothy J.; Witherington, Jason Journal of Organic Chemistry, 2006 , vol. 71, # 22 p. 8510 - 8515

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Citation Number: 28

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 ...

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