Jose M. Sansano

Palladium Catalysed Tandem Cyclisation–Anion Capture Processes. Part 4: Organotin(IV) Transfer Agents

Abstract Palladium(0) catalysed cascade mono- and bis-cyclisation–anion capture involving a wide variety of starter species, terminating species and organotin(IV) anion capture reagents are reported leading to a range of bridged, fused and spirocyclic products. The diastereoselectivity of the bis-cyclisation processes is explained in terms of steric effects in the transition states.

Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 6: Synthesis of Sugar, Nucleoside, Purine, Benzodiazepinone and β-lactam Analogues via Capture of in situ Generated Vinylstannanes

Abstract The regioselective palladium catalysed hydrostannylation of alkynes bearing a β-heteroatom affords mainly α-vinyltin(IV) compounds that are used as terminating species in palladium catalysed cyclisation–anion capture processes. The pharmacophore attached to the alkyne moiety permits the synthesis of sugars, nucleosides, purines, benzodiazepinones and β-lactams analogues in good yields.

Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 5: Cascade Hydrostannylation-bis-cyclisation-intramolecular Anion Capture. Synthesis of Bridged- and Spiro-Cyclic Small and Macrocyclic Heterocycles

A series of O- and N-α,ω-enyne derivatives of 2-iodoarylethers and 2-iodoarylamides undergo palladium catalysed cascade hydrostannylation of the ω-alkyne moiety at 0–25°C followed by bis-cyclisation at 100–110°C terminating in intramolecular sp3–sp2 Stille coupling. These cascades provide a wide range of 5/6 and 5/12–17 membered bicyclic spiro- and bridged-ring heterocycles.

SIMPLE AND EFFICIENT SYNTHESIS OF THE ACETYLENE EQUIVALENT (E)-1-BENZENESULFONYL-2-(TRIMETHYLSILYL)ETHYLENE

Abstract The acetylene equivalent (E)-1-benzenesulfonyl-2-(trimethylsilyl)ethylene is readily synthesized in a one-pot reaction, in excellent yield under very mild reaction conditions, via iodosulfonylation-dehydroiodination of vinyltrimethylsilane.