Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.
A convenient method is described for the dehydration of beta-ketoesters to generate conjugated and deconjugated alkynyl esters and conjugated allenyl esters. This sequential one-pot method involves the formation of a vinyl triflate monoanion intermediate that leads to the selective formation of alkynes or allenes depending on additives and conditions used. Product outcomes appear to be a function of unique mono- and dianion mechanisms which are described.
Maity
Pradip
P
Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431, USA.
Lepore
Salvatore D
SD
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; D000480:Alkynes; D004952:Esters; D007659:Ketones