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NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
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Davies, Alyn T., Greenhalgh, Mark D., Slawin, Alexandra M Z and Smith, Andrew D. (2020) NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides. Beilstein Journal of Organic Chemistry, 16 . pp. 1572-1578. doi:10.3762/bjoc.16.129 ISSN 1860-5397.
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Official URL: http://dx.doi.org/10.3762/bjoc.16.129
Abstract
The trifluoromethyl unit holds a prominent and privileged position within organic chemistry [1-6]. The incorporation of this motif is widely employed within the pharmaceutical, agrochemical, and materials industries as it can be used strategically to increase lipophilicity as well as to enhance metabolic stability and binding selectivity [7-9]. In this context, the generation of effective and practical methodologies capable of the enantioselective incorporation of the trifluoromethyl unit into organic molecules has been developed widely [10-12], with a series of elegant organocatalytic strategies utilized toward these aims [13]. One general strategy for the organocatalytic construction of stereogenic trifluoromethyl centers is through enantioselective addition of enolates or their equivalents to prochiral trifluoromethyl ketones (Figure 1A). Within this area, a common catalytic approach has utilized aliphatic ketones as enolate equivalents using prolinamide, cinchona, or hybrid catalysts that proceed via enamine intermediates (Figure 1B) [14-19]. The state of the art within this area has been recently demonstrated by Dixon and co-workers, who showed that bifunctional BIMP catalysts could promote the enantioselective addition of typically recalcitrant aryl ketones to trifluoromethyl ketones (Figure 1C) [20].
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
Library of Congress Subject Headings (LCSH): | Enantioselective catalysis -- Research, Ring formation (Chemistry), Heterocyclic chemistry, Carbenes (Methylene compounds), Methyl groups | |||||||||
Journal or Publication Title: | Beilstein Journal of Organic Chemistry | |||||||||
Publisher: | Beilstein-Institut | |||||||||
ISSN: | 1860-5397 | |||||||||
Official Date: | 30 June 2020 | |||||||||
Dates: |
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Volume: | 16 | |||||||||
Page Range: | pp. 1572-1578 | |||||||||
DOI: | 10.3762/bjoc.16.129 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||
Copyright Holders: | © 2020 Davies et al.; licensee Beilstein-Institut | |||||||||
Date of first compliant deposit: | 3 July 2020 | |||||||||
Date of first compliant Open Access: | 3 July 2020 | |||||||||
RIOXX Funder/Project Grant: |
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