383883-67-8Relevant academic research and scientific papers
Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage. Direct synthesis of enantiopure succinimide derivatives
Alcaide, Benito,Almendros, Pedro,Cabrero, Gema,Ruiz, M. Pilar
, p. 3981 - 3984 (2005)
(Chemical Equation Presented) Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the β-lactam nucleus. New, efficient one-pot prot
Stereoselective cyanation of 4-formyl and 4-imino-β-lactams: Application to the synthesis of polyfunctionalized γ-lactams
Alcaide, Benito,Almendros, Pedro,Cabrero, Gema,Ruiz, M. Pilar
, p. 10761 - 10768 (2013/01/15)
The stereoselective reaction of 4-oxoazetidine-2-carbaldehydes and their corresponding imines with cyanide-based reagents give β-lactam α-aminonitriles, which are chameleonic building blocks for the controlled synthesis of a variety of new compounds including functionalized γ-lactams, succinimide derivatives, and diamino-lactams derivatives in optically pure form.
Divergent reactivity of 2-azetidinone-tethered allenols with electrophilic reagents: Controlled ring expansion versus spirocyclization
Alcaide, Benito,Almendros, Pedro,Luna, Amparo,Torres, M. Rosario
supporting information; experimental part, p. 621 - 626 (2010/07/06)
A dual reactivity of 2-azetidinone-tethered allenols may occur by judicious choice of the electrophilic reagents, namely halogenating versus selenating reagents. Using common substrates, structurally different compounds, namely tetramic acids (from N-bromosuccinimide) or spirocyclic seleno-ss-lactams (from N-phenylselenophthalimide), can be readily synthesized by these divergent protocols.
