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Keywords:

  • carbenoids;
  • C[BOND]H functionalization;
  • Cope rearrangement;
  • diastereoselectivity;
  • rhodium
Thumbnail image of graphical abstract

Diastereoselectivity in control: The synthetic utility of the C[BOND]H functionalization/Cope rearrangement reaction has been greatly expanded by the design of substrates that will react through a boat transition state instead of a chair transition state. The products are formed with the opposite diastereoselectivity as previously obtained (see scheme, ABSA= acetamidobenzenesulfonylazide).