The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of delta-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cycli...

Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparat...

The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as w...

Reaction of the sulfuric acid ester of /V-hydroxy-4acetylaminobiphenyl and of the acetic acid esters of /V-hydroxy-4-acetylaminobiphenyl, /V-hydroxy-4-acetylaminostilbene, and /V-hydroxy-2-acetylaminophenanthrene with transforming DNA of Bacillus subtilis in vitro caused both inactivation of transforming activity and the induction of mutations. The parent amides, amines, /V-hydroxy amides, and ...

We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylation of the obtained amines with different acid ...

Series of chiral palladium(II) allyl and cinnamyl complexes bearing a C1-symmetric N-heterocyclic carbenes were synthesized from achiral precursors. The chirality theses results the formation carbene-palladium bond which restricts rotation dissymmetric N-aryl substituents NHC thus creates an axis chirality. Chiral HPLC at preparative scale enabled resolution racemic provided straightforward acc...