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
Synthesis of planar-chiral [2.2]paracyclophanes by biotransformations: screening for hydrolase activity for the kinetic resolution of 4-acetoxy-[2.2]paracyclophane
β 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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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
## Abstract For the preparation of the title compound, 4βhydroxy[2.2]paracyclophane (1) is first converted to the carbamate 2. Metalation of 2 with __sec__βbutyllithium yields an __ortho__βanion which after trapping with dimethylformamide and acidic workβup provides 6 in 64% yield. Further applicat