Palladium-Catalyzed C(sp3)−H Functionalization at the C3 Position of l-Pipecolinic Acid Derivatives

The study of Pd‐catalyzed arylation, alkoxylation, and acyloxylation reactions at the C3 position of l‐pipecolinic acid derivatives to afford cis‐disubstituted piperidines as single stereoisomers was performed. To demonstrate the utility of the reaction, compound 10, an analogue of (−)‐3S‐3‐PPP (9)...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2016-05, Vol.5 (5), p.608-612
Main Authors: Yu, Qun-Ying, Zhong, Hong-Ming, Sun, Wen-Wu, Zhang, Shi-Jin, Cao, Pei, Dong, Xiao-Ping, Qin, Hong-Bo, Liu, Ji-Kai, Wu, Bin
Format: Article
Language:English
Subjects:
alkoxylation
arylation
C−H activation
Organic chemistry
palladium
pipecolinic acid
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Summary:The study of Pd‐catalyzed arylation, alkoxylation, and acyloxylation reactions at the C3 position of l‐pipecolinic acid derivatives to afford cis‐disubstituted piperidines as single stereoisomers was performed. To demonstrate the utility of the reaction, compound 10, an analogue of (−)‐3S‐3‐PPP (9) that is used as a neuroleptic drug for the treatment of schizophrenia, was synthesized featuring the arylation and radical decarboxylation reactions as key steps. C3 but no PO: The study of Pd‐catalyzed arylation, alkoxylation, and acyloxylation reactions at the C3 position of l‐pipecolinic acid derivatives to afford cis‐disubstituted piperidines as single stereoisomers was performed. To demonstrate the utility of the reaction, compound 10, an analogue of (−)‐3S‐3‐PPP (9) that is used as a neuroleptic drug for the treatment of schizophrenia, was synthesized featuring the arylation and radical decarboxylation reactions as key steps.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201600072