Practical syntheses of (S)-4-hydroxytetrahydrofuran-2-one, (S)-3-hydroxytetrahydrofuran and their (R)-enantiomers

Article abstract of DOI:10.1002/jlac.199719970911

Optically active 4-hydroxytetrahydrofuran-2-one (3) has been synthesized in good yield from optically active ethyl 4-chloro-3-hydroxybutanoate (2) by refluxing with dilute hydrochloric acid. In a similar manner, optically active 3-hydroxytetrahydrofuran (5) was prepared from optically active 4-chloro-1,3-butanediol (4), which was derived from 2 by NaBH₄ reduction. These new cyclizations proceed without racemization. VCH Verlagsgesellschaft mbH, 1997.