title: Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis.
abstract: An efficient two-step synthesis of a wide range of 3-methylene-1,2-diazetidines has been developed through application of a Cu(I)-catalyzed 4-exo ring closure. The double bond of this new class of strained heterocycle can be functionalized in a stereocontrolled manner by using palladium-catalyzed Heck reactions. Moreover, chemoselective reduction of 3-alkylidene-1,2-diazetidines gives access to saturated 1,2-diazetidines and vicinal diamines.
authors.affiliation: Department of Chemistry, University of Warwick, Coventry CV4 7AL, United Kingdom.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Brown
authors.forename: Guy J
authors.initials: GJ
authors.lastname: Clarkson
authors.forename: Graham G
authors.initials: GG
authors.lastname: Inglis
authors.forename: Michael
authors.initials: M
authors.lastname: Shipman
mesh_terms: D000478:Alkylation; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001384:Azetidines; C082735:azetidine; D010165:Palladium; D003300:Copper