Asymmetric Synthesis of Six-Membered Cyclic Sulfamides via Palladium-Catalyzed Alkene Carboamination Reactions

Abstract

The asymmetric synthesis of six-membered cyclic sulfamides via palladium-catalyzed alkene carboamination reactions of N-homo­allylsulfamides with aryl halides is described. High levels of enantio­selectivity were obtained with a catalyst composed of Pd2dba3 and (S)-Siphos-PE.

Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction

“…While catalytic methods are emerging for their synthesis, most prominently proceeding through the Giese-type functionalization of an α-amino radical, these methods are fundamentally limited in terms of accessible chemical space due to the incorporation of the structural signature associated with the alkene Giese acceptor . Arguably, one of the best-established strategies toward the synthesis of α-tertiary amines is the 1,2-addition of carbon-centered nucleophiles. − However, these examples are invariably limited to activated, preformed imines. While unquestionably a powerful strategy, there are notably few examples of addition to nonactivated dialkyl imines, likely due to competitive α-deprotonation resulting from the basic nature of the organometallic nucleophile.…”

Efficient and environmentally-friendly access to 4,5-unsaturated sulfonamides through ligand-free copper-BF3-catalyzed three-component alkene carbo-sulfonamidation

“…36 For example, Wolfe and co-workers used alkene-tethered sulfonamides for carbo-sulfonamidation reaction with alkyl halide as a carbon donor, resulting in cyclic sulfonamide ring formation (Scheme 1a). 37–39…”

“…36 For example, Wolfe and co-workers used alkene-tethered sulfonamides for carbo-sulfonamidation reaction with alkyl halide as a carbon donor, resulting in cyclic sulfonamide ring formation (Scheme 1a). [37][38][39] These two-component carbo-sulfonamidation reactions were carried out in the presence of a palladium catalyst and a stoichiometric quantity of an alkoxy base. Dang et al, used alkene-tethered aromatic sulfonamides to obtain cyclic sulfonamides in the presence of large quantities of Cu(OAc) 2 , KHCO 3 as a base, and MnO 2 as an oxidant.…”