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Enantioselective Michael addition catalyzed by chiral tripodal oxazoline–tBuOK complexes

✍ Scribed by Sung-Gon Kim; Kyo Han Ahn

Book ID
104230747
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
60 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Benzene-based tripodal oxazolines are found to be novel chiral ligands for the catalytic enantioselective Michael addition via potassium enolates. Thus, methyl phenylacetate undergoes 1,4-addition to methyl acrylate using a catalytic amount of a tBuOK-oxazoline complex in toluene at -78°C, and up to 82% ee is obtained.

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Enantioselective mukaiyama-michael reactions of 2-carbomethoxy cyclopentenone catalyzed by chiral bis(Oxazoline)-Cu(II) complexes
✍ Anna Bernardi; Giorgio Colombo; Carlo Scolastico 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 236 KB

The conjugate addition of propionate silylketcne acetal 1 to 2-carbomethoxy cyclopentenone is promoted by bis(oxazoline)-Cu(ll) complexes with high diastcreosclectivity and good enantiomeric excesses. The absolute configuration of the product can bc controlled by varying the copper counterion. A ca