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Palladium‐Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations
Author(s) -
Trend Raissa M.,
Ramtohul Yeeman K.,
Ferreira Eric M.,
Stoltz Brian M.
Publication year - 2003
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.200351196
Subject(s) - chemistry , catalysis , nucleophile , alkene , palladium , organic chemistry , phenols , toluene , oxidative phosphorylation , allylic rearrangement , pyridine , phenol , medicinal chemistry , biochemistry
A variety of Pd‐catalyzed oxidative nucleophile/alkene cyclizations proceeds in excellent yield under simple aerobic conditions in nonpolar media (Pd catalyst, pyridine, and O 2 in toluene). Nucleophiles for these cyclizations include phenols, carboxylic acids, amides, and primary alcohols. Additionally, enantioselective catalysis is feasible with a Pd‐sparteine system (see picture). Enantioselectivities of up to 90 % ee are observed for simple phenol/alkene cyclizations.