1052076-50-2Relevant academic research and scientific papers
Synthesis and kinetic resolution of N-Boc-2-arylpiperidines
Cochrane, Edward J.,Leonori, Daniele,Hassall, Lorraine A.,Coldham, Iain
, p. 9910 - 9913 (2014)
The chiral base n-BuLi/(-)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39-48% and ers up to 97:3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.
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.
