A practical new asymmetric synthesis of (2S,3S)- and (2R,3R)-3-hydroxyleucine

Article abstract of DOI:10.1016/S0040-4020(01)85384-9

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.