4.8 Article

Catalytic Enantioselective [10+4] Cycloadditions

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 40, Pages 13182-13186

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807830

Keywords

asymmetric synthesis; cycloaddition; density-functional calculations; organocatalysis

Funding

  1. Carlsberg Foundation Semper Ardens
  2. Aarhus University
  3. DNRF

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The first peri- and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron-deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher-order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects.

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