Palladium‐Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations | Zendy

Trend Raissa M. | Zendy; Ramtohul Yeeman K. | Zendy; Ferreira Eric M. | Zendy; Stoltz Brian M. | Zendy

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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.

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