| Synthesis of (R)- and (S)-3,3,3-trifluoro-2-phenylpropanoyl isocyanates and their use as reactive analogues of Mosher's acid. | |
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MedLine Citation:
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PMID: 15991224 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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The title compounds have been prepared from the respective 3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acids (MTPA) by a three-step synthesis with MTPA chloride and MTPA amide as reaction intermediates. The requested compounds were obtained in high chemical yields without any change in optical purity during the preparation. To ascertain the usefulness of this auxiliary agent in the chiral analysis, isomeric 3,3,3-trifluoro-2-phenylpropanoyl isocyanates were subjected in NMR tubes to noncatalyzed reactions with 16 different commercially available chiral alcohols. The steric arrangement of all diastereomers prepared correlated well with their NMR spectral nonequivalence data (Deltadelta), thus demonstrating the regular sign distribution of Deltadelta of particular groups according to the devised molecular model. The usefulness of the novel derivatization is discussed. |
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Authors:
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Petr Vodicka; Ludvík Streinz; Jan Vávra; Bohumír Koutek; Milos Budesínský; Jan Ondrácek; Ivana Císarrová |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chirality Volume: 17 ISSN: 0899-0042 ISO Abbreviation: Chirality Publication Date: 2005 Aug |
Date Detail:
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Created Date: 2005-07-06 Completed Date: 2005-09-16 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8914261 Medline TA: Chirality Country: United States |
Other Details:
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Languages: eng Pagination: 378-87 Citation Subset: - |
Affiliation:
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Institute of Organic Chemistry and Biochemistry, Prague, Czech Republic. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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