4.7 Article

Gold Catalysis: Efficient 1,3-Induction with Diastereotopic Homopropargyl Alcohols in the Phenol Synthesis

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 14-15, Pages 2469-2481

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900402

Keywords

alkynes; arenes; cobalt; furans; gold; stereoselectivity

Funding

  1. Umicore AG Co. KG
  2. Deutsche Forschungsgemeinschaft [HA 1932/10-1]

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Furans with diastereotopic alkynyl groups were prepared and then converted to anellated phenols in gold-catalyzed reactions. In all cases a highly diastereoselective reaction was observed. The stereochemical outcome of the 1,3-induction could be assigned by two independent crystal structure analyses, showing a cis-arrangement of the two alkyl substituents on the benzoanellated cyclohexene ring.

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