An Enantioselective Approach to 4-Substituted Proline Scaffolds: Synthesis of (S)-5-(tert-Butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic Acid

Autor:	Blanca López, Martí Bartra, Ramon Berenguer, Xavier Ariza, Jordi Garcia, Roberto Gómez, Hèctor Torralvo
Jazyk:	angličtina
Rok vydání:	2020
Předmět:	phase-transfer catalysis stereoselective synthesis antiviral agent proline analogue Organic chemistry QD241-441
Zdroj:	Molecules, Vol 25, Iss 23, p 5644 (2020)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules25235644
Popis:	A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/db1f73a74a65479a8dbc9594828ed4ee Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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