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Catalytic Asymmetric Claisen Rearrangement of Enolphosphonates: Construction of Vicinal Tertiary and All-Carbon Quaternary Centers


  • Support of this research was provided by the NSF (CHE-1049551) and NIH (P50 GM086 145-01). We thank Dr. Antoni Jurkiewicz for NMR, Dr. Ian M. Steele for X-ray analysis and Dr. Furong Sun (UIUC) for MS data. Dr. David Dickson is acknowledged for his original work for this project.


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A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.

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