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Synthesis of planar-chiral [2.2]paracyclophanes by biotransformations: screening for hydrolase activity for the kinetic resolution of 4-acetoxy-[2.2]paracyclophane

✍ Scribed by Dirk Pamperin; Burghard Ohse; Henning Hopf; Markus Pietzsch


Book ID
114396362
Publisher
Elsevier Science
Year
1998
Tongue
English
Weight
65 KB
Volume
5
Category
Article
ISSN
1381-1177

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πŸ“œ SIMILAR VOLUMES


Synthesis of planar chiral [2.2]paracycl
✍ Dirk Pamperin; Henning Hopf; Christoph Syldatk; Markus Pietzsch πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 English βš– 411 KB

The synthesis of enantiomerically pure (S)-4-formyl-[2.2]paracyclophane 1 (>99% ee) and (R)-4-hydroxymethyl-[2.2]paracyclophane 2 (>78% ee) was achieved by bioreduction of (RS)-I with a yield of 49 and 34% respectively. From several microorganisms screened only a strain of the yeast Saccharomyces ce

Enzymatic kinetic resolution of (Β±)-4-ac
✍ Antonio Cipiciani; Francesco Fringuelli; Vittorio Mancini; Oriana Piermatti; Ann πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 305 KB

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. T

Planar chiral systems, IV. An efficient
✍ Hopf, Henning ;Barrett, David G. πŸ“‚ Article πŸ“… 1995 πŸ› John Wiley and Sons 🌐 English βš– 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