title: N-O tethered carbenoid cyclopropanation facilitates the synthesis of a functionalized cyclopropyl-fused pyrrolidine.
abstract: We report a facile approach to a cyclopropyl-fused pyrrolidine, which contains four stereogenic centers, by employing the N-O tethered carbenoid methodology. The synthesis was facilitated by the development of a direct Mitsunobu reaction of alcohols with N-alkyl-N-hydroxyl amides to give diazo precursors, which upon intramolecular cyclopropanation yielded a library of N-O containing cyclopropyl-fused bicyclic intermediates. Elaboration of the N-O moiety of one member of this library resulted in the formation of the desired pyrrolidine ring demonstrating the potential of this methodology for making cyclopropyl-fused heterocycles.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
authors.forename: Dimpy
authors.initials: D
authors.lastname: Kalia
authors.forename: Gökce
authors.initials: G
authors.lastname: Merey
authors.forename: Min
authors.initials: M
authors.lastname: Guo
authors.forename: Herman O
authors.initials: HO
authors.lastname: Sintim
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000577:Amides; D003521:Cyclopropanes; D011759:Pyrrolidines