ChemInform Abstract: Reactivity of tert‐Butanesulfinamides in Palladium‐Catalyzed Allylic Substitutions.

Abstract

Reactivity of tert-Butanesulfinamides in Palladium-Catalyzed Allylic Substitutions. -The process can not be applied to 1,1',2-trisubstituted alkenes such as prenyl carbonate which does not react. As exemplified on product (Vc), the sulfur atom remains configurationally stable throughout the allylation process meaning the products are enantiomerically pure. Exploitation of the tert-butylsulfinyl substituent as a stereodirecting group in the reaction with racemic allylic carbonates is hampered by significant lack of reactivity and extensive screening of conditions leads in the best case to the outcome achieved for (XII). -(MISTICO, L.; AY, E.; HUYNH, V.; BOURDERIOUX, A.; CHEMLA, F.; FERREIRA, F.; OBLE, J.; PEREZ-LUNA*, A.; POLI, G.; PRESTAT, G.; J. Organomet. Chem. 760 (2014) 124-129, http://dx.