4.6 Article

Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross-Metathesis/Intramolecular-Hydroarylation Sequence

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 5, Issue 10, Pages 2258-2265

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201000315

Keywords

enantioselectivity; heterocycles; metathesis; ruthenium; synthesis design

Funding

  1. National Science Foundation of China [20872043]
  2. Academic Leaders in Wuhan Municipality [200851430486]

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The scope of the novel ruthenium-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).

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