142075-06-7Relevant articles and documents
Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines
Gichuhi, Paul N.,Kuriyama, Masami,Onomura, Osamu
, p. 331 - 346 (2014/01/17)
A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinate
Preparation and Suzuki-Miyaura coupling reactions of tetrahydropyridine-2- boronic acid pinacol esters
Occhiato, Ernesto G.,Lo Galbo, Fabrizio,Guarna, Antonio
, p. 7324 - 7330 (2007/10/03)
A study on the conversion of lactam-derived vinyl triflates and phosphates into the corresponding vinyl boronates was carried out. While δ-valerolactam-derived vinyl triflates were successfully converted into 1,4,5,6-tetrahydropyridine-2-boronic acid pinacol ester derivatives by Pd-catalyzed coupling reaction with both bis(pinacolato)diboron and pinacolborane, pyrrolidinone and ε-caprolactam derivatives either did not react or were readily reduced. The δ-valerolactam-derived vinyl boronates are thermally stable compounds that efficiently coupled, under Pd catalysis, with structurally diverse aryl and heteroaryl bromides and triflates, vinyl iodides and bromides, and aromatic acid chlorides, to give the corresponding 2-substituted piperidines in good to excellent yields. The number of electrophiles that can virtually be coupled with these new boronic esters makes them very useful reagents for the synthesis of N-heterocyclic compounds.
The preparation of α-substituted, β-hydroxy piperidines and pyrrolidines: The total synthesis of febrifugine
Burgess, Laurence E.,Gross, Elizabeth K. M.,Jurka, Joe
, p. 3255 - 3258 (2007/10/03)
Epoxides generated from cyclic ene carbamates are effective N-acyl iminium ion precursors and allow for the preparation of β-hydroxy, α-substituted piperidines and pyrrolidines. The total synthesis of racemic Febrifugine is also described.