Kalia, DimpyMerey, GökçeGuo, MinSintim H.O.2019-05-102019-05-102013Kalia, D., Merey, G., Guo, M., & Sintim, H. O. (2013). N–O Tethered Carbenoid Cyclopropanation Facilitates the Synthesis of a Functionalized Cyclopropyl-Fused Pyrrolidine. The Journal of organic chemistry, 78(12), 6131-6142.0022-3263https://doi.org/10.1021/jo400788ahttps://hdl.handle.net/11491/589We 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. © 2013 American Chemical Society.eninfo:eu-repo/semantics/closedAccess[Belirlenecek]Article78126131614210.1021/jo400788aN/AQ2