The unprecedented annulation/hydroxyfluorination of propargylic carbamates to give 4-fluoromethyl-4-hydroxy- oxazolidinones was investigated. The reaction was effectively promoted by NaHCO3 and/or silver catalysis. The peculiar behavior of propargylic carbamates bearing a chiral steroidal moiety is described. Extensions and limitations of the procedure with respect to urea derivatives, homopropargyl compounds, internal alkynes and one-pot transformations of propargylic alcohols with isocyanates are reported.
5-Exo-dig aminocylization/hydroxyfluorination of propargylic carbamates.
Antonio Arcadi;Marco Chiarini;Luana Del Vecchio;Fabio Marinelli
2018-01-01
Abstract
The unprecedented annulation/hydroxyfluorination of propargylic carbamates to give 4-fluoromethyl-4-hydroxy- oxazolidinones was investigated. The reaction was effectively promoted by NaHCO3 and/or silver catalysis. The peculiar behavior of propargylic carbamates bearing a chiral steroidal moiety is described. Extensions and limitations of the procedure with respect to urea derivatives, homopropargyl compounds, internal alkynes and one-pot transformations of propargylic alcohols with isocyanates are reported.File in questo prodotto:
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