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.
Key words
chiral nitrone - 1,3-dipolar cycloaddition - isoxazolidines - stereocontrol - 4-hydroxyisoleucine
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