Chromium(II)-catalyzed diastereoselective pinacol type cross coupling between alpha,beta-unsaturated carbonyl compounds and aliphatic aldehydes

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2002
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Jung, Marc
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Synlett. 2002(12), pp. 2015-2018. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2002-35572
Zusammenfassung

Using only 10 mol% of CrCl2 as catalyst, acroleins and α,β-unsaturated ketones were coupled with aliphatic aldehydes to obtain substituted 1,2-diols using manganese powder as reducing agent and TMS-Cl as scavenger. Diastereoselectivities depend on the substituents especially on R1 of the unsaturated carbonyl compound. Formation of the syn-diols is preferred with sterically demanding R1, the anti-diols are obtained with smaller substituents.

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540 Chemie
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chromium, catalysis, cross-coupling, pinacols, C-C coupling
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ISO 690JUNG, Marc, Ulrich GROTH, 2002. Chromium(II)-catalyzed diastereoselective pinacol type cross coupling between alpha,beta-unsaturated carbonyl compounds and aliphatic aldehydes. In: Synlett. 2002(12), pp. 2015-2018. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2002-35572
BibTex
@article{Jung2002Chrom-9708,
  year={2002},
  doi={10.1055/s-2002-35572},
  title={Chromium(II)-catalyzed diastereoselective pinacol type cross coupling between alpha,beta-unsaturated carbonyl compounds and aliphatic aldehydes},
  number={12},
  issn={0936-5214},
  journal={Synlett},
  pages={2015--2018},
  author={Jung, Marc and Groth, Ulrich}
}
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