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Synlett 1997; 1997(SI): 491-492
DOI: 10.1055/s-1997-6111
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α-Nitrogenated Organolithium Compounds from N-(Tosylmethyl)amides

Diego A. Alonso, Emma Alonso, Carmen Nájera* , Miguel Yus1
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
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Publikationsdatum:
31. Dezember 2000 (online)

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Deprotonation of α-amido sulfones 7 with BunLi at -90°C followed by reaction with electrophiles leads, depending on the substitution on the amidic nitrogen to enamides 10 (secondary amides 7a,b) or functionalised α-amido sulfones 12 (tertiary amides 7c,d).

Naphthalene-catalysed lithiation of tertiary α-amido sulfones 7c,d in the presence of electrophiles (Barbier conditions) at -78°C affords functionalised amides 13.

α-amido sulfones - α-amido organolithium compounds - d 1 -reagents - naphthalene-catalysed lithiation