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Tandem One-Pot Biocatalytic Oxidation and Wittig Reaction in Water.

Alice J C WahartLiam N D BeardmoreRobert A FieldSebastian C CosgroveGavin J Miller
Published in: Organic letters (2024)
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.
Keyphrases
  • electron transfer
  • hydrogen peroxide
  • ionic liquid
  • nitric oxide