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Retropinacol/Cross-pinacol Coupling Reactions – A Catalytic Access to 1,2-Unsymmetrical Diols
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JoVE Journal Chemistry
Retropinacol/Cross-pinacol Coupling Reactions – A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions – A Catalytic Access to 1,2-Unsymmetrical Diols

DOI:
10.3791/51258-v

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10:12 min

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April 04, 2014

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,
1Department of Chemistry,Humboldt University of Berlin

Chapters

  • 00:05Title
  • 01:41Preparation of Titanium(IV) tert-butoxide/Triethylchlorosilane Solution and Pinacol-reaction of Tetraphenyl-1,2-ethanediol with 2-Ethylbutyraldehyde
  • 04:37Pinacol-reaction of Tetraphenyl-1,2-ethanediol with Diethyl Ketone
  • 07:12Results: Synthesis of 1,2-Unsymmetrical Diols via Retropinacol/Cross-pinacol Coupling
  • 09:43Conclusion

Summary

Automatic Translation

Automatic Translation

A novel account for the synthesis of unsymmetrical 1,2-diols based on a retropinacol/cross-pinacol coupling mechanism is described. Due to the catalytic execution of this reaction a considerable improvement compared to conventional cross-pinacol couplings is achieved.

Tags

RetropinacolCross-pinacol Coupling12-unsymmetrical DiolsCatalytic Direct Pinacol CouplingOperationally SimpleMild ConditionsRapid AccessCross-pinacol ProductsVicinal DiolsEnantioselective

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