John L. Tucker

The use of borane–amine adducts as versatile palladium-catalyzed hydrogen-transfer reagents in methanol

Abstract The scope of borane–amine adducts as reducing agents is broadened through palladium-catalyzed methanolysis capable of reducing a wide variety of functional groups. Hence, borane mediated reduction of a benzamide followed by a tandem methanolysis/hydrogenolysis of the resulting borane–benzylamine adduct allows chemoselective removal of an N -benzoyl in the presence of an O -benzoyl.

Palladium catalyzed activation of borane–amine adducts: rate enhancement of amine–borane methanolysis in the reduction of nitrobenzenes to anilines

Abstract Hydrolytically stable borane–amines can be activated in situ through palladium catalysis and perform reductions not possible otherwise. Hence, borane–trimethylamine is an efficient hydrogen-transfer reagent for the open vessel reduction of nitroaryls to anilines. Likewise, the palladium catalyzed methanolysis/decomplexation of stable borane–amine adducts is accelerated by the action of nitrobenzene.

Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center

Abstract An efficient four-step sequence has been developed for the synthesis of the κ-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific inversions at a single aziridinium stereogenic center, which leads to overall retention of stereochemistry, in a single operation. The chemistry is straightforward, practical and amenable to large-scale synthesis.

Scalable Process for 4‐(2‐Hydroxy‐2‐methyl)‐ethyl‐benzylamine

Abstract The preparation of the title compound has been revisited and improved. Starting from inexpensive cuminonitrile, 4‐(2‐hydroxy‐2‐methyl)‐ethyl‐benzylamine is obtained in a scalable two‐step process with an overall yield of 55%.