Arylhexahydroisoquinolines Made Simple

  • ChemPubSoc Europe Logo
  • Author: Saskia Neubacher
  • Published Date: 07 September 2012
  • Source / Publisher: ChemistryOpen/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Using conventional synthetic pathways, arylhexahydroquinolines are difficult to prepare. Young Keun Chung and co-workers, Seoul National University, Korea, have developed a synthetic strategy from azabicyclo[4.1.0]heptene derivatives using Rh(PPh3)2(CO)Cl/AgBF4 in 1,2-dichloroethane. The bicyclo[4.1.0]heptene derivatives are easily accessible from the corresponding cyclopropylenynes via PtCl2-catalyzed cycloisomerization. By screening different derivatives of bicyclo[4.1.0]heptenes, it became apparent that an aryl group was needed in the 1-position and a cyclopropyl group in the 6-position for efficient rearrangement to take place.

A plausible reaction mechanism is proposed.

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