Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones That Bear a Quaternary Stereocenter


  • We thank Dr. J. Craig Ruble for preliminary experiments. Support has been provided by the American Chemical Society (Organic Division Fellowship to I.D.H., sponsored by Abbott Laboratories), the National Institutes of Health (National Institute of General Medical Sciences, R01-GM57034), Merck, and Novartis. Funding for the MIT Department of Chemistry Instrumentation Facility has been furnished in part by NSF CHE-9808061 and NSF DBI-9729592.


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A common feature in indole- and benzofuran-derived natural products is a quaternary stereocenter in the 3-position of the heterocycle. The catalyst (−)-1 promotes the asymmetric synthesis of such compounds 3 (with up to 99 % ee) through the rearrangement of O-acylated benzofuranones (X=O) and oxindoles (X=NR2) 2.