Synthesis of fluorinated chirons: Stereoselective oxirane formation by reaction of diazomethane on 1-fluoro-3-arylsulfinyl-2-propanone and ring opening by selected nucleophiles
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Add time:07/27/2019 Source:sciencedirect.com
(R)-1-fluoro-3-[(4-methylphenyl)sulfinyl]-2-propanone (1) reacts with diazomethane affording (S)-2-(fluoromethyl)-2-[(R)-(4-methylphenyl)sulfinyl]methyl oxirane (2) as the main product. The influence of reaction conditions (solvent, temperature) on the chemo-and stereoselectivity has been studied. Several elaborations of 2, including reactions on the chiral auxiliary and opening of the oxirane ring by carbon, nitrogen, oxygen, phosphorus and halogen nucleophiles, are described. Full structural elucidation of the products is provided.
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