(+)‐(2R,8aR*)‐[(8,8‐Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)‐(2R,8aR*)‐[(8,8‐Dichlorocamphoryl)Sulfonyl]Oxaziridine

Abstract

(+)‐(2R,8aR*)‐[(8,8‐Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)‐(2R,8aR*)‐[(8,8‐Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)‐(3‐oxocamphorylsulfonyl)imine intermediate: (+)‐(7,7‐dimethoxy camphorylsulfonyl)imine intermediate: (+)‐(7,7‐dichlorocamphorylsulfonyl)imine product: (+)‐(2R,8aR*)‐[(8,8‐dimethoxycamphoryl)sulfonyl]oxaziridine (1) product: (−)‐(2S,8aR*)‐[(8,8‐dimethoxycamphoryl)sulfonyl]oxaziridine product: (+)‐(2R,8aR*)‐[(8,8‐dichlorocamphoryl)sulfonyl] oxaziridine (2) product: (−)‐(2S,8aR*)‐[(8,8‐dichlorocamphoryl)sulfonyl]oxaziridine

Davis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide

“…We prepared oxaziridine 1 − and used it for asymmetric sulfoxidation of rabeprazole sulfide using literature conditions, − i.e. reaction in dichloromethane or carbon tetrachloride.…”

“…We prepared oxaziridines 3 and 7 as per the procedure developed by Davis and Page. ,, Antipode of 2 was purchased from Sigma Aldrich. As shown in the experiments, initial ee obtained during reaction monitoring was further improved during work up to 97−99%.…”

Synthesis of All Diastereomers of the Piperidine−Alkaloid Substructure of Cyclopamine

“…With both enantiopure protected lactames in hand, we searched for a way to introduce the hydroxy group diastereoselectively. Finally, the treatment of the lithium enolates with 8,8-dichlorocamphoryl-sulfonyl oxaziridine (DCCSO, commercially available in both enantiomeric forms or easily prepared from the camphorsulfonic acids) proved to be ideal. Under optimized conditions, these reactions proceeded with complete diastereocontrol and a yield of 83−89% that already includes the subsequent protection as a pivaloate.…”