Synthesis of (R)- and (S)-3,3,3-trifluoro-2-phenylpropanoyl isocyanates and their use as reactive analogues of Mosher's acid
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 purit...
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Published in | Chirality (New York, N.Y.) Vol. 17; no. 7; pp. 378 - 387 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Hoboken
Wiley Subscription Services, Inc., A Wiley Company
2005
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Subjects | |
Online Access | Get full text |
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Summary: | 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 (Δδ), thus demonstrating the regular sign distribution of Δδ of particular groups according to the devised molecular model. The usefulness of the novel derivatization is discussed. Chirality 17:378–387, 2005. © 2005 Wiley‐Liss, Inc. |
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Bibliography: | istex:15CD73F8426FA49815520DC1BBB9BF7D9FA9A07C Grant Agency of the Czech Republic - No. 203/05/2141 (Research Project Z4 055 0506) ark:/67375/WNG-RNHFF76T-1 ArticleID:CHIR20176 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0899-0042 1520-636X |
DOI: | 10.1002/chir.20176 |