Asymmetric Synthesis in the Presence of Cyclodextrins |
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Authors: | Francesco Trotta Giancarlo Cravotto Stefano Rossignoli |
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Affiliation: | (1) Dipartimento di Scienza e Tecnologia del Farmaco dell'Universitá di Torino, Via Pietro Giuria 9, I-10125 Torino, Italy |
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Abstract: | Oxidative couplings of 2-naphthol, 6-bromo-2-naphthol and2-naphthylamine were achieved at room temperature in the presence of H2O2, horseradish peroxidase and a suitable cyclodextrin.2-Thionaphthol behaved differently, yielding the corresponding disulfide. Yields of binaphthyl derivatives were generally excellent, and a fairly good enantiomeric excess was observed. Under similar reaction conditions methyl 2-(6-methoxy-2-naphthyl) propanoate, when treated with esterase in the presence of cyclodextrin, yielded naproxen (a well-known anti-inflammatory drug) with a good enantiomeric excess. No reaction product was detected in the absence of cyclodextrin. Cyclodextrins do not act as simple transfer agents. |
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Keywords: | asymmetric syntheses binaphthyl enantiomers horseradish peroxidase hydrolysis naproxen |
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