Horseradish Peroxidase-Catalyzed Enantioselective Reduction of Racemic Hydroperoxy Homoallylic Alcohols: A Novel Enzymatic Method for the Preparation of Optically Active, Unsaturated Diols and Hydroperoxy Alcohols

Waldemar Adam; Michael Lazarus; Ute Hoch; Marion N. Korb; Chantu R. Saha-Möller; Peter Schreier

doi:10.1021/jo980028h

Horseradish Peroxidase-Catalyzed Enantioselective Reduction of Racemic Hydroperoxy Homoallylic Alcohols: A Novel Enzymatic Method for the Preparation of Optically Active, Unsaturated Diols and Hydroperoxy Alcohols

J Org Chem. 1998 Sep 4;63(18):6123-6127. doi: 10.1021/jo980028h.

Authors

Waldemar Adam¹, Michael Lazarus, Ute Hoch, Marion N. Korb, Chantu R. Saha-Möller, Peter Schreier

Affiliation

¹ Institutes of Organic Chemistry and of Pharmacy and Food Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.

PMID: 11672239
DOI: 10.1021/jo980028h

Abstract

The kinetic resolution of chiral diastereomeric hydroperoxy homoallylic alcohols 1 by horseradish peroxidase-catalyzed asymmetric reduction affords the optically active (R,R) or (R,S) allylic diols 2 and (S,S) or (S,R) hydroperoxy homoallylic alcohols 1 in high enantiomeric excess (up to 99%).