Direct Synthesis of Diastereomerically Pure Glycosyl Sulfonium Salts

Synthesis of diastereomerically pure nucleotide phosphoramidates.

Prodrugs of therapeutic nucleoside monophosphates masked as phosphoramidate derivatives have become an increasingly important class of antiviral drugs in pharmaceutical research for delivering nucleotides in vitro and in vivo. Conventionally, phosphoramidate derivatives are prepared as a mixture of two diastereomers. We report a class of stable phosphoramidating reagents containing an amino aci...

An efficient synthesis of imidazolinium salts using vinyl sulfonium salts.

The synthesis of imidazolinium salts from the reaction of formamidines and (2-bromoethyl)diphenylsulfonium triflate is described. A variety of symmetrical and unsymmetrical imidazolinium triflate salts were synthesized in high yield in short reaction times under mild conditions. Aromatic and aliphatic N-substituents work well. The reaction is proposed to proceed via generation of a vinyl sulfon...

Straightforward one-pot synthesis of trifluoromethyl sulfonium salts.

A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides

An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cy...

Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts.

The ligand-free trifluoromethylation of arylboronic acids with a [Ph(2)SCF(3)](+)[OTf](-)/Cu(0) system has been carefully investigated. Aryl-, alkenyl- and heteroarylboronic acids with a variety of functional groups were suitable substrates for this reaction. It is suggested that a CuCF(3) species is formed under the reaction conditions.