| Synthesis of enantiopure trifluoromethyl building blocks via a highly chemo- and diastereoselective nucleophilic trifluoromethylation of tartaric acid-derived diketones. | |
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MedLine Citation:
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PMID: 17243715 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding gamma-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two different enantiopure products: an alpha-aryl-alpha-methoxy-alpha-trifluoromethyl ethanal and an alpha-aryl-alpha-methoxycarboxylic acid. The overall process is eventually an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one. |
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Authors:
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Fabien Massicot; Nicolas Monnier-Benoit; Naba Deka; Richard Plantier-Royon; Charles Portella |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2007-01-23 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Feb |
Date Detail:
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Created Date: 2007-02-09 Completed Date: 2007-04-17 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 1174-80 Citation Subset: - |
Affiliation:
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Laboratoire Réactions Sélectives et Applications, UMR 6519 CNRS-Université de Reims Champagne-Ardenne, Faculté des Sciences, B.P. 1039, 51687 Reims Cedex 2, France. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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