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Synlett 1997; 1997(SI): 491-492
DOI: 10.1055/s-1997-6111
DOI: 10.1055/s-1997-6111
letter
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α-Nitrogenated Organolithium Compounds from N-(Tosylmethyl)amides
Further Information
Publication History
Publication Date:
31 December 2000 (online)
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