Trend, Raissa M. and Ramtohul, Yeeman K. and Ferreira, Eric M. and Stoltz, Brian M. (2003) Palladium-Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations. Angewandte Chemie International Edition, 42 (25). pp. 2892-2895. ISSN 1433-7851. doi:10.1002/anie.200351196. https://resolver.caltech.edu/CaltechAUTHORS:20170221-131404095
Full text is not posted in this repository. Consult Related URLs below.
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170221-131404095
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.
| Item Type: | Article | ||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Related URLs: |
| ||||||||||||||||
| ORCID: |
| ||||||||||||||||
| 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. | ||||||||||||||||
| Funders: |
| ||||||||||||||||
| Subject Keywords: | Asymmetric catalysis; homogeneous catalysis; oxidation; oxygen; palladium | ||||||||||||||||
| Issue or Number: | 25 | ||||||||||||||||
| DOI: | 10.1002/anie.200351196 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20170221-131404095 | ||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170221-131404095 | ||||||||||||||||
| Official Citation: | Trend, R. M., Ramtohul, Y. K., Ferreira, E. M. and Stoltz, B. M. (2003), Palladium-Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations. Angewandte Chemie International Edition, 42: 2892–2895. doi:10.1002/anie.200351196 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 74429 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | Melissa Ray | ||||||||||||||||
| Deposited On: | 21 Feb 2017 23:57 | ||||||||||||||||
| Last Modified: | 11 Nov 2021 05:27 |
Repository Staff Only: item control page
