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- W2149302673 abstract "An oxidative desulfurization-fluorination protocol has been used to synthesize (2S)-2-(difluoromethyl)-N-tosylpyrrolidine (6a) and (2S)-2-(trifluoromethyl)-N-tosylpyrrolidine (7a) from the (2S)-prolinol-derived (2S)-2-(4-chlorophenylthiomethyl)-N-tosylpyrrolidine (9) or (2S)-2-(dithian-2-yl)-N-tosylpyrrolidine (5). Efforts to prepare 3,3-difluoroalanine similarly from an N-protected S-aryl-cysteine ester 17 gave only traces of the target compound 18. Instead, an unique N-(α,α-difluorobenzyl)-N-α',α'-dibromoglycine ester 19 was formed by an unprecedented sequence of reaction steps. A plausible mechanism is suggested involving a sulfur-assisted deoxygenation-difluorination of an imino oxygen and a haloform reaction like carbon-carbon bond fission as key-steps. Efforts to prepare (2S)-2-(fluoromethyl)-N-tosylpyrrolidine (12) from (2S)-N-tosylprolinol (3) by treatment with Fluolead™ (1-tert-butyl-4-trifluorosulfanyl-3,5-dimethylbenzene) gave only 5% of the target compound, but 95% of (3R)-3-fluoro-N-tosylpiperidine (11a) by ring enlargement." @default.
- W2149302673 created "2016-06-24" @default.
- W2149302673 creator A5028580335 @default.
- W2149302673 creator A5039921470 @default.
- W2149302673 creator A5033472077 @default.
- W2149302673 date "2010-01-01" @default.
- W2149302673 modified "2023-10-13" @default.
- W2149302673 title "Oxidative desulfurization–fluorination of thioethers. Application for the synthesis of fluorinated nitrogen containing building blocks" @default.
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- W2149302673 doi "https://doi.org/10.1039/c0ob00560f" @default.
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