Solvent-Induced Chirality in the Hydroboration of Ketones

Christoph Baldauf; Nina Dickerhof; Stefan H. Hüttenhain; Stefanie Kern; Nancy Krummrich; Friedrich Kruse; Janine May; Melanie Meister; Kristina Müller; Sabine Rauer; Isabelle Salwig; Nico Scharfenecker; Birgit Spitznagel

doi:10.1071/CH08093

RESEARCH ARTICLE

Solvent-Induced Chirality in the Hydroboration of Ketones

Christoph Baldauf ^A , Nina Dickerhof ^A , Stefan H. Hüttenhain ^A ^B , Stefanie Kern ^A , Nancy Krummrich ^A , Friedrich Kruse ^A , Janine May ^A , Melanie Meister ^A , Kristina Müller ^A , Sabine Rauer ^A , Isabelle Salwig ^A , Nico Scharfenecker ^A and Birgit Spitznagel ^A

+ Author Affiliations

- Author Affiliations

^A Hochschule Darmstadt, Fachbereich Chemie und Biotechnologie, Hochschulstrasse 2, 64289 Darmstadt, Germany.

^B Corresponding author. Email: huettenhain@h-da.de

Australian Journal of Chemistry 61(6) 414-418 https://doi.org/10.1071/CH08093
Submitted: 5 March 2008 Accepted: 5 May 2008 Published: 19 June 2008

Abstract

The influence of the systematic variation of chiral solvents and of diverse Lewis acids on the asymmetric induction of the hydroboration of acetophenone has been studied. None of the solvents used could surpass lactic acid methyl ester, and for the Lewis acids, ZnCl₂ and ZnI₂ showed positive effects on the enantiomeric excess (ee) and the conversion. Also, the effect of the substrate structure was investigated by comparing the conversion and ee of eight different ketones. Apparently, the achievable asymmetric induction was higher with aromatic ketones.

Acknowledgements

We thank N. Schön for helpful discussions. S. H. Hüttenhain is grateful for financial support from the ZFE Hochschule Darmstadt.

References

Solvent-Induced Chirality in the Hydroboration of Ketones

Abstract

Acknowledgements

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