A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successful...

The structural motif of α,α-difluoro-substituted carboxyl and carbonyl groups with hydroxy- or amino-substituents at the stereogenic carbon in β-position is found frequently drugs biologically active compounds. A straightforward method for obtaining those targets high enantiomeric purity given by asymmetric difluoro-Reformatsky imino-difluoro-Reformatsky reactions that lead to α,α-difluorinated...

A novel, efficient, convenient and environmentally friendly approach for the synthesis of nitriles and imines from primary amines has been developed. Using commercially available red copper as the catalyst, ammonium bromide as the co-catalyst and molecular oxygen as the sole oxidant, nitriles and imines can be afforded in high yields through benzylic oxidation.

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles to the malonates to form nitrilium ion intermediates and subsequen...

An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free c...