Tetrahedron p. 9181 - 9188 (1994)
Update date:2022-08-04
Topics:
Hale, Karl J.
Manaviazar, Soraya
Delisser, Vern M.
A convenient new asymmetric synthesis of both enantiomers of erythro-3-hydroxyleucine is described. The key steps involve Sharpless asymmetric dihydroxylation (AD) of α,β-unsaturated ester 3, cyclic sulphate formation from the resulting diol, S(N)2 reaction with sodium azide, deesterification with aqueous sodium hydroxide, and hydrogenolysis. Utilising this route, (2S,3S)-(+)-3-hydroxyleucine (1) was obtained in 97% ee and 67% overall yield; the (2R,3R)-(-)-enantiomer was isolated in 92% ee and 57% overall yield.
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