Organische Chemie Und Biochemie

Monatshefte für Chemie / Chemical Monthly

, Volume 115, Issue 10, pp 1237-1254

First online:

Enantioselektive Cyclopropanierung von 1,1-Diphenylethylen und Diazoessigester mit Kupfer-Katalysatoren

Asymmetrische Katalysen, 21. Mitt.
  • Henri BrunnerAffiliated withInstitut für Anorganische Chemie, Universität Regensburg
  • , Wolfgang MiehlingAffiliated withInstitut für Anorganische Chemie, Universität Regensburg

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Enantioselective cyclopropanation of 1,1-diphenylethylene and diazoacetic acid ester with copper catalysts


Copper(II) compounds catalyze the reaction of 1,1-diphenylethylene with diazoacetic acid ethylester. The main product is 2,2-diphenylcyclopropane carboxylic acid ethylester. The formation of the carbene dimerization products fumaric and maleic acid diethylester can be suppressed by the continuous addition of diazoacetic acid ester to 1,1-diphenylethylene.

37 optically active ligands, partly new, were combined with copper(II)-acetate to givein-situ-catalysts. In five cases isolated copper complexes were used as catalysts. The best optical inductions in the formation of 2,2-diphenylcyclopro-pane carboxylic acid ethylester with up to 65.6% ee were achieved withSchiff base ligands, which derive from salicylaldehyde and amino alcohols, obtained from amino acid esters and phenylGrignard.


Catalytic enantioselective cyclopropanation Copper (II) catalysts Optical induction