450416-70-3Relevant academic research and scientific papers
Stereoselective synthesis of (?)-3-PPP through palladium-catalysed unactivated C(sp3)–H arylation at the C-3 position of L-pipecolinic acid
Zhang, Shi-Jin,Sun, Wen-Wu,Yu, Qun-Ying,Cao, Pei,Dong, Xiao-Ping,Wu, Bin
, p. 606 - 609 (2017)
An efficient route for the preparation of (?)-3-PPP(preclamol) using the highly stereoselective palladium-catalysed C(sp3)-H arylation and radical decarboxylation reaction as the key steps is described. The chiral center at the C-3 position of
Synthesis method of Preclamol intermediate
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Paragraph 0033; 0037-0038; 0040; 0044; 0045; 0047; 0050-0051, (2019/02/04)
The invention discloses a synthesis method of a Preclamol intermediate, comprising the following steps: carrying out a condensation reaction between N-tert-butoxycarbonyl-piperidin-3-carboxylic acid and N-hydroxy phthalimide to prepare (N-Butoxycarbonyl-p
Ligand-controlled β-selective C(sp3)-H arylation of N-Boc-piperidines
Millet, Anthony,Larini, Paolo,Clot, Eric,Baudoin, Olivier
, p. 2241 - 2247 (2013/05/22)
We report a general palladium-catalyzed β-arylation of Boc-piperidines, which yields a variety of valuable 3-arylpiperidines in a simple and direct manner. The β- vs. α-arylation selectivity was controlled by the ligand, with flexible biarylphosphines providing mainly the desired β-arylated products whereas more rigid biarylphosphines mainly furnished the more classical α-arylated products. The computed reaction mechanism (DFT), studied from the common α-palladated intermediate, indicated that the reductive elimination steps leading to the α- and β-arylated products are selectivity-determining. Moreover, the experimental trend obtained with different ligands was well reproduced by the calculations.
Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters. Enantioselective synthesis of 3-arylpiperidines
Amat, Mercedes,Canto, Margalida,Llor, Nuria,Escolano, Carmen,Molins, Elies,Espinosa, Enrique,Bosch, Joan
, p. 5343 - 5351 (2007/10/03)
Cyclodehydration of racemic γ-aryl-δ-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic δ-lactams, in a process that involves a dynamic kinetic resolution. Subsequent reduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehyde esters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and the antipsychotic drug (-)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone esters enantiopure cis-2-alkyl-3-arylpiperidines are prepared.
