As an important chiral compound, (R)-3-hydroxyl-5-hexenoate has the following chemical formula (I), where R is alkyl or cycloalkyl having 1 to 8 carbon atoms, or mono- or poly-substituted aryl or aralkyl. The compound (I) has been widely used for synthesizing chemical and chemical intermediates. For example, Chen Fener et al. (WO2016074324) disclosed an efficient route for preparing, from derivatives of the compound (1), a key chemical intermediate (III) in synthesis of statin antilipemic agents.

It is indicated by document retrieval that chemical methods are main ways of synthesizing the compound (I) and structural analogues thereof at present. For example, U.S. Pat. No. 6,355,822 disclosed a method for stereoselectively preparing 3-hydroxyl-5-hexenoate (I) by reduction of a structural analogue 3-carbonyl-5-hexenoate (II) by using the resulting product of in-situ reaction of L-tartaric acid with sodium borohydride as chiral reductant. The reduction reaction needs to be conducted at a low temperature (−20° C. to −50° C.). Such reaction condition is strict, and the practical industrial application prospect is limited.
European Patent EP1176135 disclosed a preparation method for corresponding optically pure structural analogue 3-hydroxyl-5-hexenoate (I) by asymmetric catalyzation and hydrogenation of structural analogue 3-carbonyl-5-hexenoate (II) by using a complex of ruthenium and chiral phosphine ligand. Since this reaction needs to be conducted at a high temperature and under a high hydrogen pressure, it is inconvenient for industrial production.
It was yet reported that (R)-3-hydroxyl-5-hexenoate is selectively generated by biological catalysis. For example, referring to J. Chem. Soc. Perkin. Trans. 1, 1991, 133-140, it was reported that (R)-3-hydroxyl-5-hexenoate (1) was selectively generated by catalytic reduction of the compound (II) by baker's yeast, where the ee value was 78% (methyl ester) and 43% (ethyl ester). This method is less stereoselective and is not applicable to industrial production.