Computationally Guided Stereocontrol of the Combined C[BOND]H Functionalization/Cope Rearrangement


  • This material is based on work supported by the National Science Foundation under the Center for Chemical Innovation in Stereoselective C[BOND]H Functionalization (CHE-0943980) and by the National Institutes of Health (GM080337).


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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).