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

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

Asymmetrische Katalysen, 21. Mitt.

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

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.

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Authors and Affiliations

  1. Institut für Anorganische Chemie, Universität Regensburg, D-8400, Regensburg, Bundesrepublik Deutschland

    Henri Brunner & Wolfgang Miehling

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  1. Henri Brunner
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  2. Wolfgang Miehling
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Prof. Dr.Karl Schlögl, Universität Wien, mit den besten Wünschen zum 60. Geburtstag gewidmet.

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Brunner, H., Miehling, W. Enantioselektive Cyclopropanierung von 1,1-Diphenylethylen und Diazoessigester mit Kupfer-Katalysatoren. Monatsh Chem 115, 1237–1254 (1984). https://doi.org/10.1007/BF00809355

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  • DOI: https://doi.org/10.1007/BF00809355

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