Cyclomagnesation of dienes catalyzed by a chiral ansa-zirconocene

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1998
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Inorganica Chimica Acta. 1998, 280(1-2), pp. 189-192. ISSN 0020-1693. Available under: doi: 10.1016/S0020-1693(98)00065-6
Zusammenfassung

The biphenyl-bridged, chiral zirconocene complex rac-2,2'-biphenyl-bis(3,4-dimethylcyclopentadienyl)zirconium dichloride catalyzes the reaction of 1,6- and 1,7-dienes with excess dibutyl magnesium to bis(butyl-magnesio-methyl)-substituted cycloalkane derivatives. Analogous reactions occur with butyl magnesium chloride and with heteroatom-containing dienes. The preference of 1,6-dienes for trans-fused cyclization products and that of 1,7-dienes for cis-fusion at ambient and for trans-fusion at elevated temperatures is similar to that observed before for unsubstituted zirconocene complexes. The R-enantiomer of the biphenyl-bridged zirconocene complex gives trans-fused cyclization products with an optical purity of only 15 ± 1% ee. The stereochemistry of these cyclomagnesation reactions is explained in terms of the relative rates of mutually competing cyclization and transmetalation steps.

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540 Chemie
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Ansa-zirconocene, catalysis, diene cyclomagnesation
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ISO 690MARTÍN, Sandra, Hans-Herbert BRINTZINGER, 1998. Cyclomagnesation of dienes catalyzed by a chiral ansa-zirconocene. In: Inorganica Chimica Acta. 1998, 280(1-2), pp. 189-192. ISSN 0020-1693. Available under: doi: 10.1016/S0020-1693(98)00065-6
BibTex
@article{Martin1998Cyclo-23885,
  year={1998},
  doi={10.1016/S0020-1693(98)00065-6},
  title={Cyclomagnesation of dienes catalyzed by a chiral ansa-zirconocene},
  number={1-2},
  volume={280},
  issn={0020-1693},
  journal={Inorganica Chimica Acta},
  pages={189--192},
  author={Martín, Sandra and Brintzinger, Hans-Herbert}
}
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    <dcterms:abstract xml:lang="eng">The biphenyl-bridged, chiral zirconocene complex rac-2,2'-biphenyl-bis(3,4-dimethylcyclopentadienyl)zirconium dichloride catalyzes the reaction of 1,6- and 1,7-dienes with excess dibutyl magnesium to bis(butyl-magnesio-methyl)-substituted cycloalkane derivatives. Analogous reactions occur with butyl magnesium chloride and with heteroatom-containing dienes. The preference of 1,6-dienes for trans-fused cyclization products and that of 1,7-dienes for cis-fusion at ambient and for trans-fusion at elevated temperatures is similar to that observed before for unsubstituted zirconocene complexes. The R-enantiomer of the biphenyl-bridged zirconocene complex gives trans-fused cyclization products with an optical purity of only 15 ± 1% ee. The stereochemistry of these cyclomagnesation reactions is explained in terms of the relative rates of mutually competing cyclization and transmetalation steps.</dcterms:abstract>
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