title: A new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors.
abstract: The first examples of azomethine ylides derived from allylic amine and glyoxal precursors are reported. The condensation of primary allylic and α-aryl amines with glyoxylates or α-aryl glyoxals affords conjugated azomethine ylides that undergo facile [3 + 2] cycloaddition, providing 5-alkenyl pyrrolidine cycloadducts that cannot be accessed through the classical use of amino esters as ylide precursors.
authors.affiliation: Department of Chemistry, The University of Vermont , 82 University Place, Burlington, Vermont 05405, United States.
authors.forename: Natalie K
authors.initials: NK
authors.lastname: Machamer
authors.forename: Xiaoxi
authors.initials: X
authors.lastname: Liu
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Waters
mesh_terms: D000588:Amines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D061565:Cycloaddition Reaction; D004952:Esters; D006037:Glyoxal / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000588:Amines; D001391:Azo Compounds; D004952:Esters; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D006037:Glyoxal; C032519:pyrrolidine