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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 CO bond-forming reductive elimination with retention of configuration at the carbon atom.
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Desai et al. (2007) studied this question.
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