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

Jung, Marc; Groth, Ulrich

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

Files

ChromiumII_catalyzed_diastereoselective_pinacol_type.pdf(82.71 KB)

Date

2002

Authors

Jung, Marc

Groth, Ulrich

Publication type

Journal article

Published in

Synlett ; 2002, 12. - pp. 2015-2018. - ISSN 0936-5214. - eISSN 1437-2096

Abstract

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.

Subject (DDC)

540 Chemistry

Keywords

chromium,catalysis,cross-coupling,pinacols,C-C coupling

Cite This

ISO 690

JUNG, Marc, Ulrich GROTH, 2002. Chromium(II)-catalyzed diastereoselective pinacol type cross coupling between alpha,beta-unsaturated carbonyl compounds and aliphatic aldehydes. In: Synlett(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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