The development of a series of shelf-stable monofluoroalkylated sulfonium ylide reagents and their reactions with a variety of O-nucleophiles including phenols,sulfonic acids,carboxylic acids,1-hydroxy-benzotrizoles,a...The development of a series of shelf-stable monofluoroalkylated sulfonium ylide reagents and their reactions with a variety of O-nucleophiles including phenols,sulfonic acids,carboxylic acids,1-hydroxy-benzotrizoles,amino acids was described.In general,monofluoroakylated sulfonium ylides were synthesized in three steps from commercially available starting materials including thiophenols,alkyl halides and dimethyl 2-diazomalonate.Reactions with the O-nucleophiles occurred under mild conditions and afforded the corresponding monofluoroalkylated ethers,sulfonates,and esters in good to excellent yields,thus providing a robust approach for the preparation of these compounds.Further expansion of monofluoroalkylation of C-terminus of peptides potentially provided modifieddrug-like peptides.展开更多
Enantioselective intermolecular three-component oxysulfenylations of alkenes with phenols and alcohols as O-nucleophiles were achieved using chiral BINAM-derived sulfide/phosphoric acid as the cocatalyst.Notably,chira...Enantioselective intermolecular three-component oxysulfenylations of alkenes with phenols and alcohols as O-nucleophiles were achieved using chiral BINAM-derived sulfide/phosphoric acid as the cocatalyst.Notably,chiral BINAM-derived sulfide/phosphoric acid co-catalysis was first explored to successfully catalyze highly enantioselective transformation.A variety of sulfur-containing benzylic aryl ethers and benzylic alkyl ethers,which contained two contiguous chiral stereocenters,were obtained readily in moderate to excellent yields with high to excellent enantioselectivities.展开更多
基金support from the Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)for financial support.
文摘The development of a series of shelf-stable monofluoroalkylated sulfonium ylide reagents and their reactions with a variety of O-nucleophiles including phenols,sulfonic acids,carboxylic acids,1-hydroxy-benzotrizoles,amino acids was described.In general,monofluoroakylated sulfonium ylides were synthesized in three steps from commercially available starting materials including thiophenols,alkyl halides and dimethyl 2-diazomalonate.Reactions with the O-nucleophiles occurred under mild conditions and afforded the corresponding monofluoroalkylated ethers,sulfonates,and esters in good to excellent yields,thus providing a robust approach for the preparation of these compounds.Further expansion of monofluoroalkylation of C-terminus of peptides potentially provided modifieddrug-like peptides.
基金the National Natural Science Foundation of China(NSFC)(nos.21871178,22071149,21901158,21702135)and the STCSM(no.19JC1430100)for their financial support.
文摘Enantioselective intermolecular three-component oxysulfenylations of alkenes with phenols and alcohols as O-nucleophiles were achieved using chiral BINAM-derived sulfide/phosphoric acid as the cocatalyst.Notably,chiral BINAM-derived sulfide/phosphoric acid co-catalysis was first explored to successfully catalyze highly enantioselective transformation.A variety of sulfur-containing benzylic aryl ethers and benzylic alkyl ethers,which contained two contiguous chiral stereocenters,were obtained readily in moderate to excellent yields with high to excellent enantioselectivities.
