title: LiAlH4 -Induced Selective Ring Rearrangement of 2-(2-Cyanoethyl)aziridines toward 2-(Aminomethyl)pyrrolidines and 3-Aminopiperidines as Eligible Heterocyclic Building Blocks.
abstract: 2-(2-Cyanoethyl)aziridines and 2-aryl-3-(2-cyanoethyl)aziridines were deployed as substrates for an In(OTf)3 -mediated regio- and stereoselective ring rearrangement upon treatment with LiAlH4, affording a variety of novel 2-(aminomethyl)pyrrolidines and 3-aminopiperidines, respectively. Further synthetic elaboration of the obtained 3-aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
authors.forename: Jeroen
authors.initials: J
authors.lastname: Dolfen
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
authors.forename: Karel
authors.initials: K
authors.lastname: Vervisch
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
keywords: Lewis acids; aziridines; bicyclic systems; piperidines; pyrrolidines