4.8 Article

An Asymmetric Dehydrogenative Diets-Alder Reaction for the Synthesis of Chiral Tetrahydrocarbazole Derivatives

Journal

ORGANIC LETTERS
Volume 20, Issue 1, Pages 32-35

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03251

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Funding

  1. National Natural Science Foundation of China (NNSFC) [21672049]
  2. Hefei University of Technology

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An asymmetric dehydrogenative Diets Alder reaction of 2-methyl-3-phenylmethylindoles and alpha,beta-unsaturated aldehydes has been established. The successful in situ generation of the indole ortho-quinodimethane intermediate and the iminium activation of enals are the keys to success, providing various tetrahydrocarbazole derivatives with up to >99% ee.

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