154874-91-6Relevant articles and documents
Expedient synthesis of a-heteroaryl piperidines using a pd-catalyzed suzuki cross-coupling-reduction sequence
Hesp, Kevin D.,Fernando, Dilinie P.,Jiao, Wenhua,Londregan, Allyn T.
, p. 413 - 415 (2014)
A method for the modular synthesis of a-heteroaryl piperidines is reported. The two-step procedure consists of an initial Pd-catalyzed Suzuki cross-coupling of the heteroaryl bromide with a boronate ester derived from N-Boc piperidone, followed by subsequ
Synthesis of 2-arylpiperidines by palladium couplings of aryl bromides with organozinc species derived from deprotonation of N-Boc-piperidine
Coldham, Iain,Leonori, Daniele
supporting information; experimental part, p. 3923 - 3925 (2009/05/31)
(Figure Presented) The organolithium species derived from proton abstraction of N-Boc-piperidine with s-BuLi and TMEDA can be transmetalated to the organozinc reagent, and this organometallic species can be coupled directly with aryl bromides in a Negishi-type reaction using palladium catalysis with the ligand tri-tert-butylphosphine (t-Bu3P-HBF4). The chemistry was applied to a very short synthesis of the alkaloid anabasine.
Intramolecular cyclizations of α-lithioamine synthetic equivalents: Convenient syntheses of 3-, 5-, and 6-membered-ring heterocyclic nitrogen compounds and elaborations of 3-membered ring systems
Beak,Wu,Eul Kyun Yum,Young Moo Jun
, p. 276 - 277 (2007/10/02)
A lithiation-intramolecular cyclization reaction of N-Boc chloroalkyl secondary amines is reported to provide the 2-aryl-substituted pyrrolidine and piperidines 6, 7, 9, and 11 and a series of 2-azabicyclo[3.1.0] derivatives 14-25, including cyclopropane derivatives of proline and of the indolizidine-pyrrolizidine alkaloid ring system. Lithiation-substitutions of N-Boc-N-ethylcyclopropylamine to give 27-29 and lithiation-silylations of N- Boc aziridines to give 31-33 also are reported.
