Enantioselective Partial Reduction of 2,5-Disubstituted Pyrroles via a Chiral Protonation Approach

Enantioselective Partial Reduction of 2,5-Disubstituted Pyrroles via a Chiral Protonation Approach

The partial reduction of 2,5-pyrrole diester 1 followed by enantioselective protonation in situ to furnish synthetically useful building blocks is described. An enantiomeric excess of up to 74% was achieved using (−)-ephedrine and related analogues as chiral proton sources. The pyrroline product obt...

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Veröffentlicht in:Organic letters 2004-09, Vol.6 (18), p.3055-3058
Hauptverfasser: Donohoe, Timothy J, Freestone, Graeme C, Headley, Catherine E, Rigby, Caroline L, Cousins, Rick P. C, Bhalay, Gurdip
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Combinatorial Chemistry Techniques
Ephedrine - chemistry
Indicators and Reagents
Molecular Structure
Oxidation-Reduction
Pyrroles - analysis
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
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Zusammenfassung:The partial reduction of 2,5-pyrrole diester 1 followed by enantioselective protonation in situ to furnish synthetically useful building blocks is described. An enantiomeric excess of up to 74% was achieved using (−)-ephedrine and related analogues as chiral proton sources. The pyrroline product obtained could be recrystallized to give enantiomerically pure material.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049014q