Tandem One-Pot Biocatalytic Oxidation and Wittig Reaction in Water

Wahart, Alice J. C.; Beardmore, Liam N. D.; Field, Robert A.; Cosgrove, Sebastian C.; Miller, Gavin J.

Abstract

We explore biocatalytic aldehyde generation under aqueous conditions, concomitantly delivering access to a one-pot Wittig reaction using stabilized phosphoranes and granting diverse alkene products. Using a recombinant choline oxidase mutant, we first undertake biocatalytic alcohol oxidation across a range of functional aliphatic primary alcohols, demonstrating a remarkable substrate tolerance for this enzyme, including chloride, bromide, azide, S-methyl, and alkynyl groups. Following this, we extend capability and deliver a practicable milligram-scale one-pot Wittig reaction in water.

Citation

Wahart, A. J. C., Beardmore, L. N. D., Field, R. A., Cosgrove, S. C., & Miller, G. J. (in press). Tandem One-Pot Biocatalytic Oxidation and Wittig Reaction in Water. Organic Letters, 26(31), 6642-6646. https://doi.org/10.1021/acs.orglett.4c02201

• Journal Article Type: Letter
• Acceptance Date: Jul 23, 2024
• Online Publication Date: Jul 29, 2024
• Deposit Date: Aug 12, 2024
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 26
• Issue: 31
• Pages: 6642-6646
• DOI: https://doi.org/10.1021/acs.orglett.4c02201
• Keywords: Alcohols Aldehydes Alkyls Hydrocarbons Organic reactions
• Public URL: https://keele-repository.worktribe.com/output/883352
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.orglett.4c02201