Construction of Tetrahydrofurans by PdII/PdIV-Catalyzed Aminooxygenation of Alkenes


  • This research was partially supported by the NIH NIGMS (R01 GM073836) and the Petroleum Research Fund. We also gratefully acknowledge the Arnold and Mabel Beckman Foundation as well as Abbott, Amgen, AstraZeneca, Boehringer-Ingelheim, Bristol Myers Squibb, Eli Lilly, GlaxoSmithKline, and Merck Research Laboratories for funding. L.V.D. thanks Bristol Myers Squibb for a graduate fellowship. We are also grateful to Jeff Kampf (X-ray crystallography) and Dipannita Kalyani and Kami Hull (editorial assistance).


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Resolute in the face of elimination: Substituted 3-aminotetrahydrofurans were prepared in good yield and with modest to high diastereoselectivity by the Pd-catalyzed reaction shown in the scheme (Phth=phthaloyl). Mechanistic studies indicate a PdII/PdIV catalytic cycle involving cis aminopalladation and intramolecular C[BOND]O bond-forming reductive elimination with retention of configuration at the carbon atom.