CaltechAUTHORS
Published June 24, 2003 | Version public
Journal Article Metadata-only

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

Creators

  • 1. ROR icon California Institute of Technology

Abstract

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.

Additional Information

© 2003 Wiley. Issue online 24 June 2003; version of record online 24 June 2003; manuscript received 17 February 2003. The authors wish to thank the NIH-NIGMS (R01 GM65961-01), the University of California TRDRP (postdoctoral fellowship to YKR), the NSF (predoctoral fellowship to EMF), the Dreyfus Foundation, Merck Research Laboratories, Research Corporation, and Abbott Laboratories for generous financial support. Dr. Richmond Sarpong and Mr. Julius Su are gratefully acknowledged for molecular modeling assistance.

Additional details

Identifiers

Eprint ID
74429
DOI
10.1002/anie.200351196
Resolver ID
CaltechAUTHORS:20170221-131404095

Funding

NIH
R01GM65961-01
California Tobacco-Related Disease Research Program
NSF Predoctoral Fellowship
Camille and Henry Dreyfus Foundation
Merck Research Laboratories
Research Corporation
Abbott Laboratories

Dates

Created
2017-02-21
Created from EPrint's datestamp field
Updated
2021-11-11
Created from EPrint's last_modified field