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Adam W, Mock-Knoblauch C, Saha-Möller CR. Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation. J Org Chem. 1999;64(13):4834-4839doi: 10.1021/jo990201p.
Adam, W., Mock-Knoblauch, C., & Saha-Möller, C. R. (1999). Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation. The Journal of organic chemistry, 64(13), 4834-4839. https://doi.org/10.1021/jo990201p
Adam, Waldemar, et al. "Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation." The Journal of organic chemistry vol. 64,13 (1999): 4834-4839. doi: https://doi.org/10.1021/jo990201p
Adam W, Mock-Knoblauch C, Saha-Möller CR. Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation. J Org Chem. 1999 Jun 25;64(13):4834-4839. doi: 10.1021/jo990201p. PMID: 11674558.
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J Org Chem. 1999 Jun 25;64(13):4834-4839. doi: 10.1021/jo990201p.

Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation.

The Journal of organic chemistry

Waldemar Adam, Cordula Mock-Knoblauch, Chantu R. Saha-Möller

Affiliations

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

PMID: 11674558 DOI: 10.1021/jo990201p

Abstract

The enzyme Coprinus peroxidase (CiP) was employed for the kinetic resolution of racemic hydroperoxides 1 and the asymmetric sulfoxidation of prochiral sulfides 4. Eleven hydroperoxides 1a-k were reduced by CiP and guaiacol as reductant under conditions of kinetic resolution with enantioselectivities of up to >98% for the (S)-hydroperoxide 1 and 90% for the (R)-alcohol 2. In the absence of a reductant, the hydroperoxide 1a afforded with CiP enantiomerically enriched hydroperoxide 1a (ee up to 54%) and alcohol 2a (ee up to 40%), as well as ketone 3a (which is also formed simultaneously in all other reactions) and molecular oxygen. Catalase activity was established for CiP with hydrogen peroxide. When aryl alkyl sulfides 4 were used as oxygen acceptors, three products, sulfoxides 5, alcohols 2, and hydroperoxides 1, were obtained, all in enantiomerically enriched form. The highest ee value (89%) was achieved for the sulfoxide derived from naphthyl methyl sulfide (4f). Thus, CiP may be utilized for the asymmetric synthesis of optically active hydroperoxides 1, alcohols 2, and sulfoxides 5.

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