Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates
Abstract
Here, we report asymmetric allylic alkylation of barium enolates of cyclic ketones catalyzed by a metallacyclic iridium complex containing a phosphoramidite ligand derived from (R)-1-(2-naphthyl)ethylamine. The reaction products contain adjacent quaternary and tertiary stereocenters. This process demonstrates that unstabilized cyclic ketone enolates can undergo diastereo- and enantioselective Ir-catalyzed allylic substitution reactions with the proper choice of enolate countercation. The products of these reactions can be conveniently transformed to various useful polycarbocyclic structures.
- Authors:
-
- Department of Chemistry, University of California, Berkeley, California 94720, United States
- Publication Date:
- Research Org.:
- Univ. of California, Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1163792
- Alternate Identifier(s):
- OSTI ID: 1345809
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Published Article
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Name: Journal of the American Chemical Society Journal Volume: 136 Journal Issue: 45; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Chen, Wenyong, Chen, Ming, and Hartwig, John F. Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates. United States: N. p., 2014.
Web. doi:10.1021/ja506500u.
Chen, Wenyong, Chen, Ming, & Hartwig, John F. Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates. United States. https://doi.org/10.1021/ja506500u
Chen, Wenyong, Chen, Ming, and Hartwig, John F. Thu .
"Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates". United States. https://doi.org/10.1021/ja506500u.
@article{osti_1163792,
title = {Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates},
author = {Chen, Wenyong and Chen, Ming and Hartwig, John F.},
abstractNote = {Here, we report asymmetric allylic alkylation of barium enolates of cyclic ketones catalyzed by a metallacyclic iridium complex containing a phosphoramidite ligand derived from (R)-1-(2-naphthyl)ethylamine. The reaction products contain adjacent quaternary and tertiary stereocenters. This process demonstrates that unstabilized cyclic ketone enolates can undergo diastereo- and enantioselective Ir-catalyzed allylic substitution reactions with the proper choice of enolate countercation. The products of these reactions can be conveniently transformed to various useful polycarbocyclic structures.},
doi = {10.1021/ja506500u},
journal = {Journal of the American Chemical Society},
number = 45,
volume = 136,
place = {United States},
year = {Thu Oct 30 00:00:00 EDT 2014},
month = {Thu Oct 30 00:00:00 EDT 2014}
}
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Publisher's Version of Record
https://doi.org/10.1021/ja506500u
https://doi.org/10.1021/ja506500u
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Cited by: 64 works
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Figures / Tables:
Scheme 1: Pd- and Ir-Catalyzed Allylation of Ketones
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