Sulfinimines (Thiooximine S‐Oxides): Asymmetric Synthesis of Methyl (R)‐(+)‐β‐Phenylalanate from (S)‐(+)‐N‐(Benzylidene)‐p‐Toluenesulfinamide

Sulfinimines (thiooximine s-oxides): Asymmetric synthesis of methyl (R)-(+)-β-phenylalanate from (S)-(+)-N-(benzylidene)-p-toluenesulfinamide intermediate: 10.35 g (66.8 mmol) of (S)-(+)-p-toluenesulfinamide (2) intermediate: 2.65 g (10.9 mmol) of (S)-(+)-N-(benzylidene)-p-toluenesulfinamide (3) in 50 mL of anhydrous ether intermediate: 2.13 g (6.7 mmol) of (Ss,R)-(+)-methyl N-(p-tolylsulfinyl)-3-amino-3-phenylpropanoate (4) product: methyl (R)-(+)-β-phenylalanate Keywords: addition, to CN; enamine or imine formation; hydrolysis, miscellaneous; replacement reactions, miscellaneous; stereoselective reactions, diastereoselective