Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 10, Pages 2628-2632Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309297
Keywords
asymmetric catalysis; cycloaddition; organocatalysis; spirocompounds; synthetic methods
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Funding
- European Research Council
- Science Foundation Ireland
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In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 degrees C and -30 degrees C delivering products epimeric at one stereocenter only, in near optical purity.
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