New Synthesis of Trifluoromethyl Aldimines Containing L-α-Amino Ester Moieties and Their Use in Mannich-Type Reactions

L‐α‐Amino esters were considered valuable chiral starting materials in the condensation reaction with trifluoroacetaldehyde (fluoral) ethyl hemiacetal to obtain new functionalized trifluoromethyl aldimines. Starting from these latter compounds, isovaleraldehyde was used in proline‐catalyzed Mannich‐...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2015-09, Vol.27 (9), p.571-575
Main Authors: Parise, Luca, Pelagalli, Alessia, Trulli, Laura, Vergari, Maria Cecilia, Fioravanti, Stefania, Pellacani, Lucio
Format: Article
Language:English
Subjects:
absolute configuration
Alcohols
amino acids
asymmetric synthesis
Bearing
Catalysis
Chemistry Techniques, Synthetic
chiral molecules
Chirality
Condensing
Esters
fluorinated compounds
Imines - chemical synthesis
Imines - chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
stereoselectivity
Synthesis
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Summary:L‐α‐Amino esters were considered valuable chiral starting materials in the condensation reaction with trifluoroacetaldehyde (fluoral) ethyl hemiacetal to obtain new functionalized trifluoromethyl aldimines. Starting from these latter compounds, isovaleraldehyde was used in proline‐catalyzed Mannich‐type addition reactions to give trifluoromethyl syn‐ or anti‐γ‐amino alcohols bearing the L‐α‐amino ester function, simply by changing the reaction temperature. Chirality 27:571–575, 2015. © 2015 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22478