4.8 Article

Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles by Enantioselective [2+2+2] Cycloaddition

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 5, Pages 1616-1620

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409733

Keywords

asymmetric catalysis; cycloaddition; dibenzosilole; rhodium; silicon

Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology (Japan)
  2. Asahi Glass Foundation

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A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzosiloles has been developed through a [2+2+2] cycloaddition of silicon-containing prochiral triynes with internal alkynes. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and the present catalysis is also applicable to the asymmetric synthesis of a germanium-stereogenic dibenzogermole. Preliminary studies on the optical properties of these compounds are also described.

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