Method for the synthesis of 4-hydroxyisoleucine and the derivatives thereof

摘要

The invention relates to a method for the synthesis of two isomers, at function OH, alone or in mixtures, of amino acids alpha or the derivatives thereof, having general formula (B), wherein: linkage C-O of the 4-position carbon (represented by symbol) denotes one or other of isomers III or IV, or mixtures thereof. Moreover, R₁ and R₂ represent: a hydrogen atom; or either R₁ or R₂ represents a hydrogen atom and the other substituent is a radical R_a, an acyl group -COR_a, such as acetyl, or a functional group -COOR_a, -SO₂R_a, -N (R_a, R_b), R_a and R_b, which are identical or different, representing a C1-C12 linear or branched alkyl radical, optionally substituted, an aryl group with one or more aromatic rings and heterocycles, comprising between 5 and 8C, optionally substituted, or aralkyl, the alkyl substituent and the aryl group being as defined above; or R₁ and R₂ both represent a substituent as defined above. R₃ represents a hydrogen atom or R_a and R₄ has the significance of R_a. The invention is characterised in that it comprises: the isomerisation of a compound having formula (I), wherein R₁, R₂, R_a, R₃ and R₄ are as defined above, such as to produce a compound having formula (II); and the reduction of the carbonyl function thereof which, depending on the catalytic system employed and the formula (I) compound used, produces one of the isomers having general formula (III) or (IV) or a mixture thereof having formula (B). The invention can be used for the synthesis of (2S, 3R, 4S)-4-hydroxyisoleucine.