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Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides
The synthesis of cyclic sulfamides by enantioselective Pd-catalyzed alkene carboamination reactions between N-allylsulfamides and aryl or alkenyl bromides is described. High levels of asymmetric induction (up to 95:5 e.r.) are achieved using a catalyst composed of [Pd2(dba)3] and (S)-Siphos-PE. Deuterium-labelling studies indicate the reactions proceed through syn-aminopalladation of the alkene and suggest that the control of syn- versus anti-aminopalladation pathways is important for asymmetric induction. Aminate the double bond! The enantioselective Pd-catalyzed coupling of aryl or alkenyl bromides with N-allylsulfamides affords substituted cyclic sulfamides in good yield with high levels of asymmetric induction (see scheme). The reactions proceed through stereoselective syn-aminopalladation of the alkene, which is important for high enantioselectivity.
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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method