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Organocatalytic Transfer Hydrogenation of Cyclic Enones

Tuttle, Jamison B. and Ouellet, Stéphane G. and MacMillan, David W. C. (2006) Organocatalytic Transfer Hydrogenation of Cyclic Enones. Journal of the American Chemical Society, 128 (39). pp. 12662-12663. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170427-104150733

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Abstract

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels−Alder reactions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0653066DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja0653066PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja0653066PublisherSupporting Information
Additional Information:© 2006 American Chemical Society. Received July 24, 2006. Publication Date (Web): September 8, 2006. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen, Merck, and the Astellas Foundation. S.G.O. is grateful for an NSERC fellowship.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
Astellas FoundationUNSPECIFIED
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Issue or Number:39
Record Number:CaltechAUTHORS:20170427-104150733
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170427-104150733
Official Citation:Organocatalytic Transfer Hydrogenation of Cyclic Enones Jamison B. Tuttle, Stéphane G. Ouellet, and David W. C. MacMillan Journal of the American Chemical Society 2006 128 (39), 12662-12663 DOI: 10.1021/ja0653066
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76999
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:27 Apr 2017 22:18
Last Modified:03 Oct 2019 17:52

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