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Synlett 1997; 1997(7): 761-762
DOI: 10.1055/s-1997-5784
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Enantioselective Pictet-Spengler Reaction of Nitrones Derived from N b-Hydroxytryptamine with Aldehydes Catalyzed by Chiral Brønsted Acid-Assisted Lewis Acids

Tomohiko Kawate, Hideki Yamada, Miyako Matsumizu, Atsushi Nishida, Masako Nakagawa*
  • *Faculty of Pharmaceutical Sciences, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba-shi, 263 Japan, e-mail: nakagawa@p.chiba-u.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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The enantioselective Pictet-Spengler reaction catalyzed by chiral binaphthol-derived Brønsted acid-assisted Lewis acids is demonstrated. The Pictet-Spengler reaction of nitrones, prepared from N b-hydroxytryptamine with aldehydes, gave the corresponding 1-substituted-2-hydroxytetrahydro-β-carbolines with up to 91% ee.

enantioselective Pictet-Spengler reaction - nitrones - β-carbolines - chiral Brønsted acid-assisted Lewis acids

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