Influence of chelating silyl scavengers on the diastereoselectivity of chromium catalyzed pinacol cross couplings

Fischer, Stefan; Groth, Ulrich; Jung, Marc; Lindenmaier, Marion; Vogel, Till

Influence of chelating silyl scavengers on the diastereoselectivity of chromium catalyzed pinacol cross couplings

Files

Fischer_Influence.pdf(138.5 KB)

Date

2005

Authors

Fischer, Stefan

Groth, Ulrich

Jung, Marc

Lindenmaier, Marion

Vogel, Till

Publication type

Journal article

Published in

Tetrahedron letters ; 46 (2005), 39. - pp. 6679-6682. - ISSN 0040-4039

Abstract

The choice of the silyl scavenger shows a substantial influence on the diastereoselectivity of the chromium catalyzed pinacol cross coupling. In the case of the intramolecular cyclization, two competing effects are observed. If the silylation reagents contain chelating heteroatoms in the side chain, a remarkable trans-selectivity is observed. Conversely the cis-diols are preferred if bulky substituted scavengers are used. A suitable transition state model for this reaction is reported, based on formerly published results.

Subject (DDC)

540 Chemistry

Keywords

Chromium,Catalysis,Cyclization,Pinacols,Silylation

Cite This

ISO 690

FISCHER, Stefan, Ulrich GROTH, Marc JUNG, Marion LINDENMAIER, Till VOGEL, 2005. Influence of chelating silyl scavengers on the diastereoselectivity of chromium catalyzed pinacol cross couplings. In: Tetrahedron letters. 46(39), pp. 6679-6682. ISSN 0040-4039. Available under: doi: 10.1016/j.tetlet.2005.07.142

BibTex

@article{Fischer2005Influ-10067,
  year={2005},
  doi={10.1016/j.tetlet.2005.07.142},
  title={Influence of chelating silyl scavengers on the diastereoselectivity of chromium catalyzed pinacol cross couplings},
  number={39},
  volume={46},
  issn={0040-4039},
  journal={Tetrahedron letters},
  pages={6679--6682},
  author={Fischer, Stefan and Groth, Ulrich and Jung, Marc and Lindenmaier, Marion and Vogel, Till}
}

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