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

The Journal of organic chemistry (2006-10-27)
David M Hodgson, Bogdan Stefane, Timothy J Miles, Jason Witherington
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.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
Isopropyllithium solution, 0.7 M in pentane