Communication

Manifestation of Felkin–Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids†

  1. Xing Yang1,‡,
  2. Peng Liu2,‡,
  3. Prof. K. N. Houk2,*,
  4. Prof. Vladimir B. Birman1,*

Article first published online: 22 AUG 2012

DOI: 10.1002/anie.201203327

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 38, pages 9638–9642, September 17, 2012

Additional Information

How to Cite

Yang, X., Liu, P., Houk, K. N. and Birman, V. B. (2012), Manifestation of Felkin–Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids . Angew. Chem. Int. Ed., 51: 9638–9642. doi: 10.1002/anie.201203327

Author Information

  1. 1

    Department of Chemistry, Washington University, Saint Louis, MO 63130 (USA) http://www.chemistry.wustl.edu/faculty/birman

  2. 2

    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569 (USA) http://www.chem.ucla.edu/houk

  1. ‡

    These authors contributed equally to this work.

*Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569 (USA) http://www.chem.ucla.edu/houk

  1. †

    This work was supported by the National Science Foundation (grant numbers CHE 1012979 to V.B.B. and CHE-0548209 to K.N.H.). Calculations were performed on the Hoffman2 cluster at UCLA and the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by the NSF.

  2. ‡

    These authors contributed equally to this work.

Publication History

  1. Issue published online: 13 SEP 2012
  2. Article first published online: 22 AUG 2012
  3. Manuscript Revised: 3 AUG 2012
  4. Manuscript Received: 30 APR 2012

Funded by

  • National Science Foundation. Grant Numbers: CHE 1012979, CHE-0548209
  • NSF

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (895K)

Keywords:

  • asymmetric organocatalysis;
  • enantioselective alcoholysis;
  • Felkin–Anh Model;
  • kinetic resolution;
  • stereoelectronic control
Thumbnail image of graphical abstract

Under control: The classical polar Felkin–Anh model has been applied for the first time to the analysis of diastereoselectivity in acylation reactions (see scheme). Computational studies demonstrate that stereoelectronic effects control the enantioselectivity in asymmetric catalytic alcoholysis of acyclic anhydrides.

View Full Article with Supporting Information (HTML) Get PDF (895K)