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C-H Functionalization Approach for the Synthesis of Chiral C2-Symmetric 1,5-Cyclooctadiene Ligands.

Bowen ZhangMichael R HollerbachSimon B BlakeyHuw M L Davies
Published in: Organic letters (2019)
Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed allylic C-H functionalization of COD. Either mono- or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and enantioselectivity. The double C-H functionalization generates C2-symmetric COD derivatives with four new stereogenic centers in >99% ee, which can be readily converted to a series of chiral COD ligands. Preliminary evaluations revealed that the COD ligands can be used in rhodium-catalyzed asymmetric arylation of cyclohex-2-enone, leading to the conjugate addition products in up to 76% ee.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • room temperature
  • mass spectrometry