4.8 Article

Rhodium-Catalyzed Enantioselective N-Allylation of Sulfoximines

Journal

ORGANIC LETTERS
Volume 25, Issue 16, Pages 2756-2760

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00414

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N-functionalization of free sulfoximines is a significant method for modifying their properties for various applications. This study presents a rhodium-catalyzed N-allylation of free sulfoximines (=NH) with allenes, enabling chemo- and enantioselective ?-hydroamination of allenes and gem-difluoroallenes. The synthesis of sulfoximine products using this method is also demonstrated.
The N-functionalization of free sulfoximines is an important approach to modifying their chemical and biological properties for downstream applications. Here, we report a rhodium-catalyzed N-allylation of free sulfoximines (=NH) with allenes under mild conditions. The redox-neutral and base-free process enables chemo-and enantioselective ?-hydroamination of allenes and gem-difluoroallenes. Synthetic applications of sulfoximine products obtained thereof have been demonstrated.

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