Alkyl 2-(2-benzothiazolylsulfinyl)acetates as useful synthetic reagents for alkyl 4-hydroxyalk-2-enoates by sulfinyl-Knoevenagel reaction

Isopropyl, ethyl, and methyl 2-(2-benzothiazolylsulfinyl)acetates have been found to be useful synthetic reagents for sulfinyl-Knoevenagel reaction with various aldehydes to give directly the corresponding 4-hydroxyalk-2-enoates [R′CH(OH)CHCHCO2R], which are ubiquitous structures in biologically active natural products and useful building blocks for organic synthesis of chiral compounds. From the optically pure (R)-2-(2-benzothiazolylsulfinyl)acetates (>99% ee) prepared by the enzymatic kinetic resolution of (±)-2-(2-benzothiazolylsulfinyl)acetates, optically active 4-hydroxyalk-2-enoates (up to 91% ee) have been obtained in good yields.