1092462-35-5Relevant articles and documents
Mg(ClO4)2-catalyzed intramolecular allylic amination: Application to the total synthesis of demethoxyfumitremorgin C
Jiang, Danfeng,Xu, Zhengren,Jia, Yanxing
experimental part, p. 4225 - 4232 (2012/07/14)
A Mg(ClO4)2-catalyzed intramolecular amination of allylic alcohols with carbamate or sulfonamide nucleophiles to form substituted piperidine and pyrrolidine derivatives has been developed. This method has been successfully applied to the total synthesis of demethoxyfumitremorgin C.
FeCl3-catalyzed highly diastereoselective synthesis of substituted piperidines and tetrahydropyrans
Guerinot, Amandine,Serra-Muns, Anna,Gnamm, Christian,Bensoussan, Charlelie,Reymond, Sebastien,Cossy, Janine
supporting information; experimental part, p. 1808 - 1811 (2010/10/03)
The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
An efficient synthesis of 2- and 2,6-substituted piperidines using Pd II-catalyzed 1,3-chirality transfer reaction
Hande, Sudhir M.,Kawai, Nobuyuki,Uenishi, Jun'ichi
supporting information; experimental part, p. 244 - 253 (2009/04/11)
(Chemical Equation Presented) An efficient and general method for 2- and 2,6-substituted piperidine syntheses using PdII-catalyzed 1,3-chirality transfer reaction has been developed. The various N-protected ζ-amino allylic alcohols cyclize in the presence of PdCl 2(CH3CN)2 to give substituted piperidines with high stereoselectivities. The syntheses of (S)-(+)- and (R)-(-)-coniine were achieved in 3 steps from the optically pure allylic alcohols (S)-14c and (R)-14c, respectively. Although the rates of reactions were significantly accelerated in CH2Cl2, THF gave the highest stereoselectivity. PdCl2(CH3CN)2 was found to be the best catalyst for this transformation. A plausible reaction pathway involving the formation of the Pd π-complex directed by the chiral secondary allylic alcohol followed by syn-azapalladation, and subsequent syn-elimination of PdCl(OH) is proposed.