Asymmetric syntheses of trans-3,4-disubstituted 2-piperidinones and piperidines

Autor:	Yuh-Sheng Wen, Hsiang-Ling Huang, Lee Tai Liu, Chia-Lin Jeff Wang, Shyh-Fong Chen, Pao-Chiung Hong
Rok vydání:	2001
Předmět:	Inorganic Chemistry Acylation chemistry Organic Chemistry ALUMINUM HYDRIDE chemistry.chemical_element Lithium Physical and Theoretical Chemistry Alkylation Combinatorial chemistry Catalysis
Zdroj:	Tetrahedron: Asymmetry. 12:419-426
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(01)00069-6
Popis:	A convenient and practical method for the preparation of chiral 4-aryl-2-piperidinone from 3-arylglutaric anhydride and (S)-methylbenzylamine is described. Acylation or alkylation at the α-carbon of the chiral 4-aryl-2-piperidinone product afforded chiral trans-3,4-disubstituted 2-piperidinone derivatives and reduction of the chiral 2-piperidinones with lithium aluminum hydride provided the corresponding enantiomerically pure trans-3,4-disubstituted piperidines. This methodology has been successfully applied to the synthesis of the anti-depressant paroxetine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::48a0b9359954eb903d5c8ec7dba952d2 https://doi.org/10.1016/s0957-4166(01)00069-6 Zobrazit plný text záznamu Full Text from ScienceDirect