Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
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| Authors: | Rebecca L. Grange Elizabeth A. Clizbe Emma J. Counsell P. Andrew Evans |
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| Affiliation: | a Queen''s University , Department of Chemistry , 90 Bader Lane , Kingston , ON K7L 3N6 , Canada . Email: ; b The University of Liverpool , Department of Chemistry , Crown Street , Liverpool , L69 7ZD , UK |
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| Abstract: | 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. |
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