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1,3-Dipolar cycloaddition of a chiral nitrone to (E)-1,4-dichloro-2-butene: a new efficient synthesis of (2S,3S,4R)-4-hydroxyisoleucine
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1,3-Dipolar cycloaddition of a chiral nitrone to (E)-1,4-dichloro-2-butene: a new efficient synthesis of (2S,3S,4R)-4-hydroxyisoleucine

Kaiss Aouadi, Erwann Jeanneau, Moncef Msaddek and Jean-Pierre Praly
Tetrahedron letters, Vol.53(23), pp.2817-2821
06/06/2012
DOI: https://doi.org/10.1016/j.tetlet.2012.03.110

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
1,3-Dipolar cycloaddition of a chiral nitrone derived from (-)-menthone to (E)-1,4-dichlorobut-2-ene was the key step in a novel 5 step synthesis of (2S,3S,4R)-4-hydroxyisoleucine, obtained in 21% overall yield with high enantiopurity. (C) 2012 Elsevier Ltd. All rights reserved.

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