Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides: A Possible Intermediate Characterized

Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides: A Possible Intermediate Characterized

Two 1:1 noncovalent mixed aggregates between a lithium enolate and two diastereomeric lithium amides have been identified spectroscopically in THF. The NMR data, as well as DFT theoretical calculations, shine some light on a puzzling reversal of induction, observed when switching from one diastereom...

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Veröffentlicht in:Organic letters 2009-05, Vol.11 (9), p.1907-1910
Hauptverfasser: Lecachey, Baptiste, Duguet, Nicolas, Oulyadi, Hassan, Fressigné, Catherine, Harrison-Marchand, Anne, Yamamoto, Yasutomo, Tomioka, Kiyoshi, Maddaluno, Jacques
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Catalysis
Chemical Sciences
Lithium - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Organometallic Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Two 1:1 noncovalent mixed aggregates between a lithium enolate and two diastereomeric lithium amides have been identified spectroscopically in THF. The NMR data, as well as DFT theoretical calculations, shine some light on a puzzling reversal of induction, observed when switching from one diastereomer of the amide to the other in the enantioselective Michael addition of the lithium enolate to an unsaturated ester.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900275y