Diastereoselective Synthesis of 2‑Phenyl-3-(trifluoromethyl)piperazines as Building Blocks for Drug Discovery

The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert–Prakash reagent (TMSCF3) to α-amino sulfinylimines bearing Ellman’s auxiliary. This methodology allows a...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-06, Vol.79 (12), p.5887-5894
Main Authors: Sánchez-Roselló, María, Delgado, Oscar, Mateu, Natalia, Trabanco, Andrés A, Van Gool, Michiel, Fustero, Santos
Format: Article
Language:English
Subjects:
Catalysis
Drug Discovery
Hydrocarbons, Fluorinated - chemistry
Indicators and Reagents - chemistry
Molecular Structure
Piperazines - chemical synthesis
Piperazines - chemistry
Silanes - chemistry
Stereoisomerism
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Summary:The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert–Prakash reagent (TMSCF3) to α-amino sulfinylimines bearing Ellman’s auxiliary. This methodology allows an entry into hitherto unknown trifluoromethylated and stereochemically defined piperazines, key scaffold components in medicinal chemistry.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500832j