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Practical Syntheses of (S)-4-Hydroxytetrahydrofuran-2-one, (S)-3-Hydroxytetrahydrofuran and Their (R)-Enantiomers

✍ Scribed by Yuasa, Yoshifumi ;Tsuruta, Haruki

Book ID: 102366871
Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 271 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970911

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✦ Synopsis

Abstract

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 NaBH~4~ reduction. These new cyclizations proceed without racemization.

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