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Enzymatic kinetic resolution of (±)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase. An efficient route for the preparation of (+)-R-4-hydroxy- and (+)-S-4-acetoxy[2.2]paracyclophane

✍ Scribed by Antonio Cipiciani; Francesco Fringuelli; Vittorio Mancini; Oriana Piermatti; Anna Maria Scappini; Renzo Ruzziconi

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 305 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00758-8

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✦ Synopsis

The enzymatic kinetic resolution of (-+)-4-acetoxy122]paracyclophane by Candida cylindracea lipase was investigated in water and in a two-phase aqueous organic system. The (+)-(R)-4-hydroxy-and (+)-(S)-4-acetoxyl2,2l-paracyclophanes were isolated in excellent yields and high enantiomeric excesses. The resolution was carried oul on multi-gram scale in hexane-water at 40 ° C.

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Planar chiral systems, IV. An efficient

Planar chiral systems, IV. An efficient route for the preparation of 5-formyl-4-hydroxy[2.2]paracyclophane (FHPC)

✍ Hopf, Henning ;Barrett, David G. 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 289 KB

## Abstract For the preparation of the title compound, 4‐hydroxy[2.2]paracyclophane (1) is first converted to the carbamate 2. Metalation of 2 with __sec__‐butyllithium yields an __ortho__‐anion which after trapping with dimethylformamide and acidic work‐up provides 6 in 64% yield. Further applicat