Amat Mercedes, Cantó Margalida, Llor Núria, Escolano Carmen, Molins Elies, Espinosa Enrique, Bosch Joan
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
J Org Chem. 2002 Jul 26;67(15):5343-51. doi: 10.1021/jo025894f.
Cyclodehydration of racemic gamma-aryl-delta-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic delta-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.
外消旋γ-芳基-δ-氧代酯与(R)-或(S)-苯甘醇进行环脱水反应，通过动态动力学拆分过程立体选择性地生成双环δ-内酰胺。这些内酰胺随后的还原反应得到对映体纯的3-芳基哌啶。从外消旋醛酯出发，这一简短序列已应用于(R)-3-苯基哌啶和抗精神病药物(-)-3-PPP（一种(S)-3-芳基哌啶）的合成，而从外消旋酮酯出发，则可制备对映体纯的顺式-2-烷基-3-芳基哌啶。
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