1235984-58-3Relevant academic research and scientific papers
N-O tethered carbenoid cyclopropanation facilitates the synthesis of a functionalized cyclopropyl-fused pyrrolidine
Kalia, Dimpy,Merey, Goekce,Guo, Min,Sintim, Herman O.
supporting information, p. 6131 - 6142 (2013/07/26)
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.
Remote C-H functionalization: Using the N-O moiety as an atom-economical tether to obtain 1,5- and the rare 1,7-C-H insertions
Wang, Jingxin,Stefane, Bogdan,Jaber, Deana,Smith, Jacqueline A.I.,Vickery, Christopher,Diop, Mouhamed,Sintim, Herman O.
supporting information; experimental part, p. 3964 - 3968 (2010/09/03)
(Chemical Equotion Present) Dr. N-O: Rhodium-catalyzed intramolecular C-H insertion with diazocompounds, which are tethered by alkoxyamines, afforded 1,5- and the rare 1,7-insertion products (see scheme; Bn = benzyl). The resulting N-O tether is unaffected under the C-H insertion reaction conditions and it can be readily cleaved or transformed into various functionalities. The reduction of the N-O moiety controls acyclic stereochemistry.
