Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines.
نویسندگان
چکیده
We have devised a highly regio- and enantioselective iridium-catalyzed allylic amination reaction with the sulfur-stabilized aza-ylide, S,S-diphenylsulfilimine. This process provides a robust and scalable method for the construction of aryl-, alkyl- and alkenyl-substituted C-chiral allylic sulfilimines, which are important functional groups for organic synthesis. Additionally, the combination of the allylic amination with an in situ deprotection of the sulfilimine constitutes a convenient one-pot protocol for the construction of chiral nonracemic primary allylic amines.
منابع مشابه
Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc01317d Click here for additional data file.
1. General Information All reactions were carried out in flame-dried glassware under an atmosphere of argon or nitrogen using anhydrous solvent. Dichloromethane was dried by passage through activated alumina columns. n-Propylamine was distilled from activated zinc dust and stored over sodium hydroxide. All other reagents were purchased from Acros, Aldrich, Alfa Aesar or Strem and used as receiv...
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ورودعنوان ژورنال:
- Chemical science
دوره 6 1 شماره
صفحات -
تاریخ انتشار 2015