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- W2911556321 abstract "Abstract We herein report the unprecedented synthesis of diverse biologically important aza‐heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur‐based aza‐ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α‐imino gold carbenes by N−S cleavage of sulfilimines. These gold carbenes undergo C−H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3‐azabicyclo[3.1.0]hexan‐2‐imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold‐catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza‐heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α‐imino gold carbenes. Moreover, an unexpected synthesis of 4‐acylquinolines (3 examples) from 2‐acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2‐hydride shift onto the α‐imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered." @default.
- W2911556321 created "2019-02-21" @default.
- W2911556321 creator A5005258392 @default.
- W2911556321 creator A5012490798 @default.
- W2911556321 creator A5034392272 @default.
- W2911556321 creator A5041749592 @default.
- W2911556321 creator A5067884400 @default.
- W2911556321 creator A5084670164 @default.
- W2911556321 date "2019-01-31" @default.
- W2911556321 modified "2023-10-16" @default.
- W2911556321 title "Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles" @default.
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