Skip to main content
SpringerLink
Log in

Synthesis of Optically Active α-Methyl β-Hydroperoxy Esters by Diastereoselective Singlet Oxygen Ene Reaction and Horseradish Peroxidase Catalyzed Kinetic Resolution

  • Contributions
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

 Optically active diastereomeric β-hydroperoxy esters 4 have been prepared by singlet oxygen ene reaction of β,γ-unsaturated esters 3 and subsequent horseradish peroxidase (HRP) catalyzed kinetic resolution of the ene product. The highest enantiomeric excess (up to 95%) has been obtained for the isopropyl ester threo-4c, which establishes that the size of the remote ester functionality exercises appreciable control in the enantioselectivity of the enzymatic kinetic resolution.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Author information

Authors and Affiliations

  1. Institut für Organische Chemie der Universität Würzburg, D-97074 Würzburg, Germany, , , , , , DE

    Waldemar Adam, Chantu R. Saha-Möller & Oliver Weichold

Authors
  1. Waldemar Adam
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chantu R. Saha-Möller
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Oliver Weichold
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Received December 20, 1999. Accepted (revised) February 11, 2000

Rights and permissions

Reprints and permissions

About this article

Cite this article

Adam, W., Saha-Möller, C. & Weichold, O. Synthesis of Optically Active α-Methyl β-Hydroperoxy Esters by Diastereoselective Singlet Oxygen Ene Reaction and Horseradish Peroxidase Catalyzed Kinetic Resolution. Monatshefte fuer Chemie 131, 697–705 (2000). https://doi.org/10.1007/s007060070098

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s007060070098

Search

Navigation