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New Synthetic Routes toward Enantiopure (2S,3R,4R)-4-Hydroxyisoleucine by 1,3-Dipolar Cycloaddition of a Chiral Nitrone to C4 Alkenes
Journal article   Peer reviewed

New Synthetic Routes toward Enantiopure (2S,3R,4R)-4-Hydroxyisoleucine by 1,3-Dipolar Cycloaddition of a Chiral Nitrone to C4 Alkenes

Kaiss Aouadi, Erwann Jeanneau, Moncef Msaddek and Jean-Pierre Praly
Synthesis (Stuttgart), Vol.2007(21), pp.3399-3405
02/11/2007
DOI: https://doi.org/10.1055/s-2007-990802

Abstract

paper
Abstract 1,3-Dipolar cycloaddition reaction of a chiral nitrone derived from (-)-menthone to E/Z mixtures of crotonaldehyde or (Z)-but-2-en-1,4-diol opens, by simultaneous creation of three contiguous asymmetric centers, new access to enantiopure (2S,3R,4R)-4-hydroxyisoleucine, respectively in 13% (7 steps) and 34% (6 steps) overall yield.

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