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Title: 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:
 [1];  [1];  [1]
  1. Univ. of California, Berkeley, CA (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 Volume: 136; Journal Issue: 45; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
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. doi:10.1021/ja506500u.
Chen, Wenyong, Chen, Ming, and Hartwig, John F. Wed . "Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: Synergetic effect of ligands and barium enolates". United States. doi: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 = {2014},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1021/ja506500u

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Cited by: 35 works
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Works referencing / citing this record:

CCDC 1427097: Experimental Crystal Structure Determination: GUSSOE : (2-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)(phenyl)acetaldehyde
dataset, September 2015

  • Chen, Wenyong; Chen, Ming; Hartwig, John F.
  • Cambridge Structural Database (CSD)
  • DOI: 10.5517/cc1jx0dv