title: Formal aminocyanation of α,β-unsaturated cyclic enones for the efficient synthesis of α-amino ketones.
abstract: Installation of amino functionality on organic molecules through direct CN bond formation is an important research objective. To achieve this goal, a 1,2-aminocyanation reaction was developed. The reaction occurs through the formation of pyrazolines by means of a formal dipolar cycloaddition of cyclic α,β-unsaturated ketones with lithium trimethylsilyldiazomethane followed by novel protonolytic N-N bond cleavage under mild conditions. This two-step process provides a diverse array of structurally complex free and mono-alkylated α-amino ketones in excellent yields.
authors: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL, 60607 (USA).
authors: Chunrui
authors: C
authors: Sun
authors: Matthew J
authors: MJ
authors: O'Connor
authors: Daesung
authors: D
authors: Lee
authors: Donald J
authors: DJ
authors: Wink
authors: Robert D
authors: RD
authors: Milligan
mesh_terms: D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003486:Cyanides; D007659:Ketones
keywords: NN bond cleavage; aminocyanation; cycloaddition; trimethylsilyldiazomethane; α-amino ketones