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Construction of Tetrahydrofurans by Pd II /Pd IV ‐Catalyzed Aminooxygenation of Alkenes
Author(s) -
Desai Lopa V.,
Sanford Melanie S.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701454
Subject(s) - catalysis , reductive elimination , intramolecular force , yield (engineering) , chemistry , medicinal chemistry , palladium , catalytic cycle , carbon fibers , stereochemistry , organic chemistry , materials science , composite number , metallurgy , composite material
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 Pd II /Pd IV catalytic cycle involving cis aminopalladation and intramolecular CO bond‐forming reductive elimination with retention of configuration at the carbon atom.