Nucleophilic substitution a t tetracoordinate, hexavalent sulfur is shown to occur with inversion at sulfur. Oxidation of (S)-N-methylbenzenesulfinamide (1) with chlorine gave (R)-,Vi-methylbenzenesulfonimidoyl chloride ( 3 ) (retention at sulfur). Reaction of 3 with sodium phenoxide gave (S)-phenyl N-methylbenzenesulfonimidate (5) (inversion). Methyllithium and 5 gave (S)-N,S-dimethyl-S-phenylsulfoximine (4) (inversion). Reduction of 4 with aluminum amalgam gave 1. The reactions of alkyllithiums with phenyl benzenesulfonimidate provide sulfoximines that are difficult or impossible to prepare by standard methods.
Asymmetric Reduction of Phosphinyl Imines with Hydride Reagents. Enantioselective Synthesis of Chiral Primary Amines Summary: Prochiral diphenylphosphinyl imines are asymmetrically reduced by chiral hydride reagents to chiral diphenylphosphinylamines. For dialkyl examples, the enantioselectivities obtained are the highest thus far for hydride reductions of imine derivatives.
Es werden verschiedene Substitutionsreaktionen an Sulfonimidoyl‐Verbindungen unter Erhalt der Konfiguration durchgeführt und die Strukturen durch Querbeziehungen sichergestellt.
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