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Asymmetric catalysis, part 91: Enantioselective monophenylation ofcis-1,2-cyclopentanediol with triphenylbismuth diacetate and chiral copper(II) complexes as catalysts

Asymmetrische Katalysen, 91. Mitt.: Enantioselektive Monophenylierung voncis-1,2-Cyclopentandiol mit Triphenylwismutdiacetat und chiralen Kupfer(II)-Komplexen als Katalysatoren

  • Anorganische Und Physikalische Chemie
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Summary

The monophenylation ofcis-1,2-cyclopentanediol with triphenylbismuth diacetate in the presence of chiral Cu(II) complexes as catalysts gavecis-2-hydroxy-1-phenoxy-cyclopentane with enantiomeric excesses up to 38%. The optically active ligands used were triamine derivatives of 2,6-bis(aminomethyl)pyridine and diamine derivatives of 2-(aminomethyl)pyridine. Selectivity in the monophenylation occurred only in the presence of the latter as auxiliary ligands.

Zusammenfassung

Die Monophenylierung voncis-1,2-Cyclopentandiol mit Triphenylwismutdiacetat in Gegenwart chiraler Cu(II)-Komplexe als Katalysatoren ergabcis-2-Hydroxy-1-phenoxy-cyclopentan mit Enantiomerenüberschüssen von bis zu 38%. Die eingesetzten optisch aktiven Liganden waren Triamin-Derivate von 2,6-bis(Aminomethyl)pyridin und Diamin-Derivate von 2-(Aminomethyl)pyridin. Selektivität bei der Monophenylierung war nur in Gegenwart letzterer als Auxiliar-Liganden zu beobachten.

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  1. Institut für Anorganische Chemie, Universität Regensburg, D-93040, Regensburg, Deutschland

    H. Brunner & T. Chuard

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  1. H. Brunner
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  2. T. Chuard
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Brunner, H., Chuard, T. Asymmetric catalysis, part 91: Enantioselective monophenylation ofcis-1,2-cyclopentanediol with triphenylbismuth diacetate and chiral copper(II) complexes as catalysts. Monatsh Chem 125, 1293–1300 (1994). https://doi.org/10.1007/BF00811078

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  • DOI: https://doi.org/10.1007/BF00811078

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