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Enantioselective Organocatalytic α-Fluorination of Aldehydes

Beeson, Teresa D. and MacMillan, David W. C. (2005) Enantioselective Organocatalytic α-Fluorination of Aldehydes. Journal of the American Chemical Society, 127 (24). pp. 8826-8828. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170512-125249442

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Abstract

The first direct enantioselective catalytic α-fluorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective fluorination of aldehydes to generate α-fluoro aldehydes, an important chiral synthon for medicinal agent synthesis. The use of imidazolidinone 1 as the asymmetric catalyst has been found to mediate the fluorination of a large variety of aldehyde substrates with N-fluorobenzenesulfonimide serving as the electrophilic source of fluorine. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 20 mol % were generally employed in this study, successful halogenation can be accomplished using catalyst loadings as low as 2.5 mol %.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja051805fDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja051805fPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja051805fPublisherSupporting Information
Additional Information:© 2005 American Chemical Society. Received March 21, 2005. Publication Date (Web): May 19, 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. Mike Brochu is thanked for experimental efforts.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
Issue or Number:24
Record Number:CaltechAUTHORS:20170512-125249442
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170512-125249442
Official Citation:Enantioselective Organocatalytic α-Fluorination of Aldehydes Teresa D. Beeson and David W. C. MacMillan Journal of the American Chemical Society 2005 127 (24), 8826-8828 DOI: 10.1021/ja051805f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77416
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:12 May 2017 23:30
Last Modified:03 Oct 2019 17:57

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