Asymmetric Amplification in Catalysis by trans-1,2-Diaminocyclohexane Bistriflamide

Asymmetric Amplification in Catalysis by trans-1,2-Diaminocyclohexane Bistriflamide

A strong asymmetric amplification is observed in the addition of diethylzinc on aromatic aldehydes in the presence of the bistriflamide of trans-1,2-diaminocyclohexane 3a. The asymmetric amplification originates from the insolubility of the catalyst precursor 3a of low enantiomeric excess (ee), with...

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Veröffentlicht in:Organic letters 2007-01, Vol.9 (2), p.251-253
Hauptverfasser: Satyanarayana, Tummanapalli, Ferber, Benoit, Kagan, Henri B
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemical synthesis
Alcohols - chemistry
Aldehydes - chemistry
Catalysis
Cyclohexylamines - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Stereoisomerism
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Zusammenfassung:A strong asymmetric amplification is observed in the addition of diethylzinc on aromatic aldehydes in the presence of the bistriflamide of trans-1,2-diaminocyclohexane 3a. The asymmetric amplification originates from the insolubility of the catalyst precursor 3a of low enantiomeric excess (ee), with a concomitant large increase of ee for the minor soluble part of 3a. Controlled mono-N-acetylation of 3a (20% ee) at −78 °C allowed isolation of 4 possessing 90% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062653b