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

Abstract

The invention relates to a method for the synthesis of two isomers, at function OH, alone or in mixtures, of amino acids α 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, Rand Rrepresent: a hydrogen atom; or either Ror Rrepresents a hydrogen atom and the other substituent is a radical R, an acyl group —COR, such as acetyl, or a functional group —COOR, —SOR, —N (R, R), Rand R, 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 Rand Rboth represent a substituent as defined above. Rrepresents a hydrogen atom or Rand Rhas the significance of R. The invention is characterised in that it comprises: the isomerisation of a compound having formula (I), wherein R, R, R, Rand Rare 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.