Asymmetric Bromolactonization Catalyzed by a C₃‐Symmetric Chiral Trisimidazoline

A productive alliance: In an enantioselective organocatalytic bromolactonization of 5‐substituted hex‐5‐enoic acids (see scheme), it appears that the formation of an ion pair through interaction of the trisimidazoline catalyst 1 with the substrate both creates a chiral environment and promotes the c...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-11, Vol.49 (48), p.9174-9177
Hauptverfasser: Murai, Kenichi, Matsushita, Tomoyo, Nakamura, Akira, Fukushima, Shunsuke, Shimura, Masato, Fujioka, Hiromichi
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Sprache:eng
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Zusammenfassung:A productive alliance: In an enantioselective organocatalytic bromolactonization of 5‐substituted hex‐5‐enoic acids (see scheme), it appears that the formation of an ion pair through interaction of the trisimidazoline catalyst 1 with the substrate both creates a chiral environment and promotes the cyclization by activating the carboxylic acid. DBDMH=1,3‐dibromo‐5,5‐dimethylhydantoin.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201005409