Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles.
A stereoselective and high-yield synthesis of hexahydropyrrolo[3,4-b]pyrroles from tetramic acids and 2H-azirines under Cu(I)-NHC catalysis is developed. An unusual N-C2 azirine bond cleavage, initiated by a copper enolate, was rationalized in terms of a free radical reaction mechanism.
Institute of Chemistry, Saint-Petersburg State University , Universitetskii pr. 26, 198504 St. Petersburg, Russia.
Nikolai V
NV
Rostovskii
Institute of Chemistry, Saint-Petersburg State University , Universitetskii pr. 26, 198504 St. Petersburg, Russia.
Pavel A
PA
Sakharov
Institute of Chemistry, Saint-Petersburg State University , Universitetskii pr. 26, 198504 St. Petersburg, Russia.
Mikhail S
MS
Novikov
Institute of Chemistry, Saint-Petersburg State University , Universitetskii pr. 26, 198504 St. Petersburg, Russia.
Alexander F
AF
Khlebnikov
Institute of Chemistry, Saint-Petersburg State University , Universitetskii pr. 26, 198504 St. Petersburg, Russia.
Galina L
GL
Starova
D001389:Azirines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism
D001389:Azirines; D007454:Iodides; D011758:Pyrroles; D011760:Pyrrolidinones; C009435:tetramic acid; D003300:Copper; C073870:cuprous iodide