Enantioselective mukaiyama-michael reactions of 2-carbomethoxy cyclopentenone catalyzed by chiral bis(Oxazoline)-Cu(II) complexes

✍ Scribed by Anna Bernardi; Giorgio Colombo; Carlo Scolastico

• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 236 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02048-5

✦ Synopsis

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 catalytic version of the reaction was developed, which gave ketoacid Sa in 72% d.e. and 63% e.e.