Communication

Iron-Catalyzed Asymmetric Olefin cis-Dihydroxylation with 97 % Enantiomeric Excess†

  1. Ken Suzuki Dr.2,
  2. Paul D. Oldenburg Dr.1,
  3. Lawrence Que Jr. Prof. Dr.1

Article first published online: 31 JAN 2008

DOI: 10.1002/anie.200705061

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 10, pages 1887–1889, February 22, 2008

Additional Information

How to Cite

Suzuki, K., Oldenburg, P. and Que, L. (2008), Iron-Catalyzed Asymmetric Olefin cis-Dihydroxylation with 97 % Enantiomeric Excess. Angewandte Chemie International Edition, 47: 1887–1889. doi: 10.1002/anie.200705061

Author Information

  1. 1

    Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN 55455, USA, Fax: (+1) 612-624-7029

  2. 2

    Research & Development Division, Takasago International Corporation, 1-4-11 Nishi-yawata, Hiratsuka, Kanagawa 254-0073, Japan

  1. †

    This work was supported by the US Department of Energy (DOE DE-FG02-03ER15455) and the Takasago Corporation. We would like to acknowledge Dr. Victor G. Young, Jr., and the X-Ray Crystallographic Laboratory of the University of Minnesota for solving the structures of complexes 1–3.

Publication History

  1. Issue published online: 15 FEB 2008
  2. Article first published online: 31 JAN 2008
  3. Manuscript Received: 1 NOV 2007

Funded by

  • US Department of Energy. Grant Number: DOE DE-FG02-03ER15455
  • Takasago Corporation

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Keywords:

  • asymmetric catalysis;
  • dihydroxylation;
  • iron;
  • N ligands;
  • oxidation

Graphical Abstract

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Bigcis-ster: The use of an (R,R)-bipyrrolidine backbone with two α-methylpyridine pendant arms affords a tetradentate N4 ligand that coordinates an iron center with cis-α topology (see picture; Fe purple, C gray, N blue, O red, S yellow, F green). This complex catalyzes the reaction between H2O2 and cis-2-heptene to afford a cis-diol product in very high enantioselectivity.

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